Chloroform → HCID 86734688, compound

HRID 329020

Reaction equation

HRID 329020 reaction equation
C(N(CC)CC)C.[CH2:8]1[C@@H:18]2[C@H:12]([CH:13]=[CH:14][C:15]3[C:16]4[N:17]2[C:19]2[CH:28]=[CH:27][N:26]=[CH:25][C:20]=2[C:21]=4[CH2:22][CH2:23][CH:24]=3)[CH2:11][CH2:10][CH2:9]1.C(Cl)(Cl)Cl.[CH:33]1([C:39](Cl)=[O:40])[CH2:38][CH2:37][CH:36]=[CH:35][CH2:34]1>O>[CH:33]1([C:39]([CH:10]2[CH2:11][CH:12]3[CH:13]=[CH:14][C:15]4[C:16]5[N:17]([C:19]6[CH:28]=[CH:27][N:26]=[CH:25][C:20]=6[C:21]=5[CH2:22][CH2:23][CH:24]=4)[CH:18]3[CH2:8][CH2:9]2)=[O:40])[CH2:38][CH2:37][CH:36]=[CH:35][CH2:34]1

Participants

6

Reactant 4

HCID 6212Chloroform2×HCID 8471TriethylamineHCID 5230583-Cyclohexene-1-carbonyl chlorideHCID 86734686(+/-)-trans-1,2,3,4,4a,8,9,14a-Octahydropyrido[4',3':2,3]indolo[1,7-ab][1]benzazepine

Product 1

HCID 86734688HCID 86734688, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triethylamine (10 ml.) was added with stirring to a solution of 5.5 g. (±)-trans-1,2,3,4,4a,8,9,14a-octahydropyrido[4',3':2,3]indolo[1,7-ab][1]benzazepine in 100 ml. chloroform, followed by addition, with stirring, of 5.76 g. (0.04 moles) 3-cyclohexene-1-carbonyl chloride in 10 ml. chloroform. The mixture was refluxed 2 hours then cooled and water was added. The organic layer was separated, dried over K2CO3, and evaporated to dryness in vacuo. Trituration of the residual oil in hexane gave (±)-trans-3-[(3-cyclohexen-1-yl)carbonyl]-1,2,3,4,4a,8,9,14a-octahydropyrido[4',3':2,3]indolo[1,7-ab][1]benzazepine, m.p. 156.5°-158.5° .

Workup

  1. stirringwith stirring, of 5.76 g
  2. temperatureThe mixture was refluxed 2 hours
  3. temperaturethen cooled
  4. customThe organic layer was separated
  5. dry with materialdried over K2CO3
  6. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-0a572bf32bce4963be8dbc8130dcf586
Source dataset
uspto-grants-1977_04
Patent number
US04018930

Linked notes

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