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N,N-Dimethylaniline → 3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-ylcarbonyl)-1-benzylpiperidine hydrogen oxalate hemihydrate

HRID 323696
Notes
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Reaction equation

HRID 323696 reaction equation
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15](Cl)=[O:16])[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.[C:42]([OH:47])(=[O:46])[C:43]([OH:45])=[O:44]>C(O)C.CC(C)=O.C1(C)C=CC=CC=1>[OH2:16].[C:42]([OH:47])(=[O:46])[C:43]([OH:45])=[O:44].[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:11]3[CH2:12][CH2:13][CH2:14][N:9]([CH2:2][C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=4)[CH2:10]3)=[O:16])[C:22]=2[CH:21]=[CH:20][CH:19]=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:11]3[CH2:12][CH2:13][CH2:14][N:9]([CH2:2][C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=4)[CH2:10]3)=[O:16])[C:22]=2[CH:21]=[CH:20][CH:19]=1.[C:42]([OH:47])(=[O:46])[C:43]([OH:45])=[O:44]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 949N,N-DimethylanilineHCID 971Oxalic AcidHCID 10308IminodibenylHCID 220062041-Benzyl-3-piperidinecarbonyl chloride hydrochloride

Product 1

HCID 1317224903-(10,11-dihydro-5H-dibenz[b,f]azepin-5-ylcarbonyl)-1-benzylpiperidine hydrogen oxalate hemihydrateYield 39%

Reagents, catalysts & solvents

3
HCID 180AcetoneSolventHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of 1-benzyl-3-piperidinecarbonyl chloride hydrochloride (12.5 g, 45.6 mmol), 10,11-dihydro-5H-dibenz[b,f]azepine (8.9 g, 45.6 mmol), N,N-dimethylaniline (15 ml) and toluene (100 ml) was heated at reflux temperature for 14 h. The mixture was decanted and to the remaining solid 10% ammonia (100 ml) and chloroform (100 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 gradient chromatography on silica gel (200 g) using benzene and chloroform as eluents. The chloroform fractions afforded the crude product. This was dissolved in ethanol (30 ml) and neutralised with oxalic acid in acetone, affording 8.8 g (39%) of 3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-ylcarbonyl)-1-benzylpiperidine hydrogen oxalate hemihydrate.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 14 h
  3. customThe mixture was decanted and to the remaining solid 10% ammonia (100 ml) and chloroform (100 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 gradient chromatography on silica gel (200 g)
  9. customThe chloroform fractions afforded the crude product

Sources & evidence

ORD record
ord-23e0c2ad46d14ebd92bb5f3115dccfc6
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06214816B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes