p-Anisoyl chloride → [2-(Dimethylaminophenylmethyl)cyclohexyl]4-methoxybenzoate hydrochloride

HRID 1596034Notes

Reaction equation

HRID 1596034 reaction equation
COC1C=CC(C([Cl:9])=O)=CC=1.C(N(CC)CC)C.CN(C(C1C=CC=CC=1)C1CCCCC1O)C.[OH-].[K+].[CH3:38][N:39]([CH:41]([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[CH:42]1[CH2:47][CH2:46][CH2:45][CH2:44][CH:43]1[O:48][C:49](=[O:58])[C:50]1[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][CH:51]=1)[CH3:40]>C(Cl)Cl>[ClH:9].[CH3:38][N:39]([CH:41]([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[CH:42]1[CH2:47][CH2:46][CH2:45][CH2:44][CH:43]1[O:48][C:49](=[O:58])[C:50]1[CH:51]=[CH:52][C:53]([O:56][CH3:57])=[CH:54][CH:55]=1)[CH3:40]

Participants

7

Reactant 5

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 9929165[2-(Dimethylaminophenylmethyl)-cyclohexyl]4-methoxybenzoateHCID 112647962-(Dimethylaminophenylmethyl)cyclohexanol

Product 1

HCID 9953026[2-(Dimethylaminophenylmethyl)cyclohexyl]4-methoxybenzoate hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.06 g (6.43 mmole) of 4-methoxybenzoyl chloride were dissolved in 4 ml methylene chloride, and 870 mg (8.57 mmole) triethylamine were added at −10° C. (methanol/ice cooling bath). 1.0 g (4.29 mmole) of the 2-(dimethylamino-phenylmethyl)cyclohexanol prepared according to Example 2 (1st stage), dissolved in 2 ml methylene chloride, was then added dropwise, and the mixture was subsequently stirred for 15 hours. For working up, 2 ml potassium hydroxide solution (0.5 N) were added, and the organic phase was separated, dried over sodium sulfate, filtered and concentrated on a rotary evaporator (500 to 10 mbar). 1.78 g of crude base were obtained. 1.00 g of the hydrochloride of [2-(dimethylaminophenylmethyl)-cyclohexyl]4-methoxybenzoate (58% of theoretical) with a melting point above 230° C. was obtained from the crude base in accordance with Example 1 (4th stage) using chlorotrimethylsilane/water in 2-butanone.

Workup

  1. additionwas then added dropwise
  2. customthe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated on a rotary evaporator (500 to 10 mbar)
  6. custom1.78 g of crude base were obtained

Sources & evidence

ORD record
ord-a0a3161135f0446cbd7cf570a103cea7
Source dataset
uspto-grants-2001_09
Patent number
US06288278B1

Reaction notes

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