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

HRID 323696

反応式

HRID 323696 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-23e0c2ad46d14ebd92bb5f3115dccfc6
出典データセット
uspto-grants-2001_04
特許番号
US06214816B1

関連ノート

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