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Benzoyl chloride → N-(4-benzyl-4-dimethylaminocyclohexyl)-N-propylbenzamide hydrochloride

HRID 1179037
Notes
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Reaction equation

HRID 1179037 reaction equation
[CH3:1][N:2]([CH3:19])[C:3]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7][CH:6]([NH:9][CH2:10][CH2:11][CH3:12])[CH2:5][CH2:4]1.[CH2:20](N(CC)CC)C.[C:27]([Cl:35])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[OH-].[K+]>C(Cl)Cl.CN(C1C=CN=CC=1)C.O>[ClH:35].[CH2:13]([C:3]1([N:2]([CH3:1])[CH3:19])[CH2:4][CH2:5][CH:6]([N:9]([CH2:10][CH2:11][CH3:12])[C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:7][CH2:8]1)[C:18]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 9856507N,N-dimethyl-1-phenyl-N'-propyl-cyclohexane-1,4-diamine

Product 1

HCID 69338285N-(4-benzyl-4-dimethylaminocyclohexyl)-N-propylbenzamide hydrochloride

Reagents, catalysts & solvents 3

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 962WaterSolvent
HCID 6344DichloromethaneSolvent

Procedure

1.00 g of the nonpolar diastereomer of N,N-dimethyl-1-phenyl-N′-propyl-cyclohexane-1,4-diamine (see example 6) were dissolved in 15 ml methylene chloride, and 560 μl triethylamine and approx. 10 mg DMAP were added. 468 μl benzoyl chloride were added dropwise, while cooling in an ice/methanol bath, and the reaction mixture was then stirred overnight, while warming to room temperature. For working up, 12 ml five molar KOH solution and 12 ml water were added, the mixture was stirred for ten minutes and extracted three times with 25 ml methylene chloride each time, the combined extracts were dried over magnesium sulfate and filtered and the filtrate was concentrated. From the product obtained (1.31 g), 1.01 g of the nonpolar diastereomer of N-(4-benzyl-4-dimethylamino-cyclohexyl)-N-propyl-benzamide hydrochloride were prepared as described for example 1 with water and chlorotrimethylsilane in 2-butanone.

Workup

  1. temperaturewhile cooling in an ice/methanol bath
  2. stirringthe mixture was stirred for ten minutes
  3. extractionextracted three times with 25 ml methylene chloride each time
  4. dry with materialthe combined extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c045560f5c294e1b97d3cb09b3f774c0
Source dataset
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07276518B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes