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

HRID 323696

반응식

HRID 323696 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 180Acetone용매HCID 702Ethanol용매HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-23e0c2ad46d14ebd92bb5f3115dccfc6
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06214816B1

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