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

HRID 323698

反応式

HRID 323698 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-88a4d356da2349a5b1d876b9ed2e1347
出典データセット
uspto-grants-2001_04
特許番号
US06214816B1

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