Hydrochloric Acid → HCID 9863763, compound

HRID 2188372Notes

Reaction equation

HRID 2188372 reaction equation
[Mg].Br[C:3]1[CH:14]=[CH:13][C:6]([O:7]C(OCC)C)=[CH:5][CH:4]=1.[CH3:15][N:16]([CH:18]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][C:20]1=[O:25])[CH3:17].[Cl-:32].[NH4+].Cl>O1CCCC1.CCOCC>[ClH:32].[CH3:17][N:16]([CH:18]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][C:20]1([C:3]1[CH:4]=[CH:5][C:6]([OH:7])=[CH:13][CH:14]=1)[OH:25])[CH3:15]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 27237611-bromo-4-(1-ethoxyethoxy)benzeneHCID 5462224MagnesiumHCID 111722992-(Dimethylaminophenylmethyl)cyclohexanone

Product 1

HCID 9863763HCID 9863763, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
55 °C

Procedure

0.38 g (15.5 mmole) of magnesium turnings was stirred in 5 ml of tetrahydrofuran of analysis purity. 3.81 g (15.5 mmole) of 1-(4-bromophenoxy)-1-ethoxyethane dissolved in 5 ml of tetrahydrofuran were added dropwise so that the reaction mixture boiled gently. After completion of the addition the reaction mixture was stirred for a further hour at 55° C. 3.0 g (13.0 mmole) of the 2-(dimethylaminophenylmethyl)cyclohexanone prepared according to Example 1 were dissolved in 15 ml of tetrahydrofuran, added dropwise to the Grignard reagent while cooling in an ice bath, and stirred for 15 hours at RT. The reaction mixture was worked up by adding 30 ml of saturated ammonium chloride solution while cooling in an ice bath, and was extracted three times at RT, each time with 80 ml of ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated on a rotary evaporator (500 to 10 mbar). 5.25 g of crude base were obtained, which were dissolved in 20 ml of ether followed by the addition of 10 ml of hydrochloric acid (1 N). The aqueous phase was separated and sufficient sodium bicarbonate was added to adjust the pH to ca. 8.The base was extracted three times, each time with 20 ml of ether, and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated by evaporation on a rotary evaporator (500 to 10 mbar). 1.96 g of crude base (46.3% of theory) were obtained, from which 1.8 g of 4-[2-(dimethylaminophenylmethyl)-1-hydroxycyclohexyl]phenol, hydrochloride were obtained (38.6% of theory) with 0.49 ml of hydrochloric acid (32 m %,) and 20 ml of acetone. The hydrochloride decomposes on heating above 140° C.

Workup

  1. additionwere added dropwise so that the reaction mixture
  2. additionAfter completion of the addition the reaction mixture
  3. temperaturewhile cooling in an ice bath
  4. stirringstirred for 15 hours at RT
  5. temperaturewhile cooling in an ice bath
  6. extractionwas extracted three times at RT
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated on a rotary evaporator (500 to 10 mbar)
  10. custom5.25 g of crude base were obtained
  11. customThe aqueous phase was separated
  12. additionsufficient sodium bicarbonate was added
  13. extractionwas extracted three times
  14. dry with materialeach time with 20 ml of ether, and the combined organic extracts were dried over sodium sulfate
  15. filtrationfiltered
  16. concentrationconcentrated by evaporation on a rotary evaporator (500 to 10 mbar)

Sources & evidence

ORD record
ord-a8521bc916b6442f89248e434f33fa82
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

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