Benzoyl chloride → HCID 10155696, compound

HRID 1179042Notes

Reaction equation

HRID 1179042 reaction equation
[CH2:1]([C:8]1([N:17]([CH3:19])[CH3:18])[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][CH3:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(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>[CH2:1]([C:8]1([N:17]([CH3:19])[CH3:18])[CH2:13][CH2:12][CH:11]([N:14]([CH2:15][CH3:16])[C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:35].[CH2:1]([C:8]1([N:17]([CH3:19])[CH3:18])[CH2:13][CH2:12][CH:11]([N:14]([CH2:15][CH3:16])[C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 69337829HCID 69337829, compound

Product 2

HCID 10155696HCID 10155696, compoundHCID 69337858HCID 69337858, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3.00 g 1-benzyl-N′-ethyl-N,N-dimethyl-cyclohexane-1,4-diamine were dissolved in 50 ml methylene chloride, and 1.68 ml triethylamine and approx. 10 mg DMAP were added. 1.40 ml 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, 50 ml five molar KOH solution and 50 ml water were added, the mixture was stirred for ten minutes and extracted three times with 50 ml methylene chloride each time, the combined extracts were dried over magnesium sulfate and filtered and the filtrate was concentrated. The crude product obtained (4.05 g) was chromatographed over silica gel with methanol/ether 1:1. 1.09 g of the polar diastereomer of N-(4-benzyl-4-dimethylamino-cyclohexyl)-N-ethyl-benzamide were obtained, from which 1.01 mg of the corresponding 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 50 ml methylene chloride each time
  4. dry with materialthe combined extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe crude product obtained (4.05 g)
  8. customwas chromatographed over silica gel with methanol/ether 1:1

Sources & evidence

ORD record
ord-f6d6c5ea2a6e48149ae2a69e216a9f06
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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