N,N-Dimethylaniline → 4-((10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)carbonyl)-1-benzylpiperidine

HRID 323698

Reaction equation

HRID 323698 reaction equation
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][CH:12]([C:15](Cl)=[O:16])[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:18]1[C:28]2[CH2:27][CH2:26][C:25]3[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=3[NH:23][C:22]=2[CH:21]=[CH:20][CH:19]=1.CN(C)C1C=CC=CC=1>C1(C)C=CC=CC=1>[CH:18]1[C:28]2[CH2:27][CH2:26][C:25]3[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=3[N:23]([C:15]([CH:12]3[CH2:13][CH2:14][N:9]([CH2:2][C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=4)[CH2:10][CH2:11]3)=[O:16])[C:22]=2[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 10308IminodibenylHCID 192613541-Benzyl-4-piperidinecarbonylchloride hydrochloride

Product 1

HCID 192613554-((10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)carbonyl)-1-benzylpiperidineYield 36.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-benzyl-4-piperidinecarbonylchloride hydrochloride (25.0 g, 91 mmol), 10,11-dihydro-5H-dibenzo[b,f]azepine (17.6 g, 90 mmol), N,N-dimethylaniline (25 ml) and toluene (150 ml) was heated at reflux temperature under stirring for 14 h. The mixture was decanted and to the remaining solid 10% ammonia (100 ml) and chloroform (150 ml) were added. The phases were separated and the combined toluene and chloroform phases were dried (K2CO3) and evaporated in vacuo. The residue was purified by chromatography on silica gel (300 g) using benzene and ethyl acetate as eluents. The crude base was crystallised from cyclohexane, yielding 13.0 g (36%) of 4-((10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)carbonyl)-1-benzylpiperidine.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature
  3. customThe mixture was decanted and to the remaining solid 10% ammonia (100 ml) and chloroform (150 ml)
  4. additionwere added
  5. customThe phases were separated
  6. dry with materialthe combined toluene and chloroform phases were dried (K2CO3)
  7. customevaporated in vacuo
  8. customThe residue was purified by chromatography on silica gel (300 g)
  9. customThe crude base was crystallised from cyclohexane

Sources & evidence

ORD record
ord-88a4d356da2349a5b1d876b9ed2e1347
Source dataset
uspto-grants-2001_04
Patent number
US06214816B1

Linked notes

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