4-Bromoanisole → HCID 9885975, compound

HRID 2188365Notes

Reaction equation

HRID 2188365 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.[CH3:11][N:12]([CH:14]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C:16]1=[O:21])[CH3:13].[Cl-:28].[NH4+]>O1CCCC1>[ClH:28].[CH3:13][N:12]([CH:14]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C:16]1([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1)[OH:21])[CH3:11]

Participants

6

Reactant 4

HCID 77304-BromoanisoleHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 111722992-(Dimethylaminophenylmethyl)cyclohexanone

Product 1

HCID 9885975HCID 9885975, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

0.88 g (36.3 mmole) of magnesium turnings was stirred in 10 ml of tetrahydrofuran of analysis purity. 4.55 ml (36.3 mmole) of 4-bromoanisole dissolved in 30 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 RT. 7.0 g (30.3 mmole) of 2-(dimethylaminophenylmethyl)cyclohexanone prepared according to Example 1 were dissolved in 10 ml of tetrahydrofuran, added dropwise to the Grignard reagent while cooling in an ice bath, and stirred for 15 hours at RT. The reaction solution was worked up by adding 40 ml of saturated ammonium chloride solution while cooling in an ice bath, and extracted three times at RT with in each case 100 ml of ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered and concentrated by evaporation on a rotary evaporator (500 to 10 mbar). 10.5 g of crude base (102% of theory) were obtained. 4.24 g of 2-(dimethylaminophenylmethyl)-1-(4-methoxyphenyl)cyclohexanol, hydrochloride (37.2% of theory) were obtained from the crude base according to the procedure described in Example 1 (3rd stage) with chlorotrimethylsilane/water in 2-butanone. The hydrochloride decomposes on heating above 150° 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. extractionextracted three times at RT with in each case 100 ml of ethyl acetate
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated by evaporation on a rotary evaporator (500 to 10 mbar)
  10. custom10.5 g of crude base (102% of theory) were obtained

Sources & evidence

ORD record
ord-7d2b133edcae421992591068339b4354
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

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