Benzoyl chloride → HCID 10132608, compound

HRID 1179040Notes

Reaction equation

HRID 1179040 reaction equation
[CH2:1]([C:8]1([N:16]([CH3:18])[CH3:17])[CH2:13][CH2:12][CH:11]([NH:14][CH3:15])[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:26]([Cl:34])(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[OH-].[K+]>C(Cl)Cl.CN(C1C=CN=CC=1)C.O>[CH2:1]([C:8]1([N:16]([CH3:18])[CH3:17])[CH2:13][CH2:12][CH:11]([N:14]([CH3:15])[C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:34].[CH2:1]([C:8]1([N:16]([CH3:18])[CH3:17])[CH2:13][CH2:12][CH:11]([N:14]([CH3:15])[C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=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 69338491HCID 69338491, compound

Product 2

HCID 10132608HCID 10132608, compoundHCID 69336941HCID 69336941, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3.00 g 1-benzyl-N,N,N′-trimethyl-cyclohexane-1,4-diamine were dissolved in 50 ml methylene chloride, and 1.78 ml triethylamine and approx. 10 mg DMAP were added. 1.41 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 (3.61 g) was chromatographed over silica gel with methanol/ether 1:1. 231 mg of the polar diastereomer of N-(4-benzyl-4-dimethylamino-cyclohexyl)-N-methyl-benzamide were obtained, from which 188 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 (3.61 g)
  8. customwas chromatographed over silica gel with methanol/ether 1:1

Sources & evidence

ORD record
ord-887a448d8ba64fd28c3612783f3fe1d2
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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