Ammonium Chloride → HCID 9821745, compound

HRID 2188390Notes

Reaction equation

HRID 2188390 reaction equation
[Mg].[CH3:2][O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][Cl:9])=[CH:6][CH:5]=1.[CH3:12][N:13]([CH:15]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C:17]1=[O:22])[CH3:14].[Cl-].[NH4+]>O1CCCC1>[ClH:9].[CH3:14][N:13]([CH:15]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C:17]1([CH2:8][C:7]1[CH:10]=[CH:11][C:4]([O:3][CH3:2])=[CH:5][CH:6]=1)[OH:22])[CH3:12]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 699934-Methyloxybenzyl chlorideHCID 5462224MagnesiumHCID 111722992-(Dimethylaminophenylmethyl)cyclohexanone

Product 1

HCID 9821745HCID 9821745, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
65 °C

Procedure

0.38 g (15.6 mmole) of magnesium turnings was stirred in 15 ml of tetrahydrofuran of analysis purity. 2.44 g (15.6 mmole) of 4-methoxybenzyl chloride dissolved in 15 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 1.5 hours at 65° 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 while cooling in an ice bath to the Grignard reagent, and stirred for 15 hours at RT. The reaction mixture was worked up by adding 20 ml of saturated ammonium chloride solution while cooling in an ice bath, and extracted three times at RT with 20 ml of ether each time. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated by evaporation on a rotary evaporator (500 to 10 mbar). 4.26 g of crude base (93.0% of theory) were obtained, from which 2.87 g of 2-(di-methylaminophenylmethyl)-1-(4-methoxybenzyl)cyclohexanol, hydrochloride (56.8% of theory) were obtained according to the procedure described in Example 1 (3rd Stage) with chlorotrimethylsilane/water in 2-butanone. The hydrochloride decomposes on heating above 130° C.

Workup

  1. additionwere added dropwise so that the reaction mixture
  2. additionAfter completion of the addition the reaction mixture
  3. additionadded dropwise
  4. stirringstirred for 15 hours at RT
  5. temperaturewhile cooling in an ice bath
  6. extractionextracted three times at RT with 20 ml of ether each time
  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)

Sources & evidence

ORD record
ord-e4919c193f16441ba7189298bb7416b1
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

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