Dichloromethane → HCID 70633015, compound

HRID 329017Notes

Reaction equation

HRID 329017 reaction equation
[CH2:1]1[C:11]2[N:10]3[C:12]4[CH:21]=[CH:20][N:19]=[CH:18][C:13]=4[C:14]4[CH2:15][CH2:16][CH:17]=[C:8]([C:9]=43)[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3][CH2:2]1.ClCCl.[CH:25]1([C:28](Cl)=[O:29])[CH2:27][CH2:26]1>C(N(CC)CC)C>[CH:25]1([C:28]([CH:3]2[CH2:4][C:5]3[CH:6]=[CH:7][C:8]4[C:9]5[N:10]([C:12]6[CH:21]=[CH:20][N:19]=[CH:18][C:13]=6[C:14]=5[CH2:15][CH2:16][CH:17]=4)[C:11]=3[CH2:1][CH2:2]2)=[O:29])[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 77637Cyclopropanecarbonyl chlorideHCID 67838308HCID 67838308, compound

Product 1

HCID 70633015HCID 70633015, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 16.4 g of 1,2,3,4,8,9-hexahydropyrido[4',3':2,3]indolo[1,7-ab][1]benzazepine in 500 ml. of dichloromethane, 7.3 g. of cyclopropanecarbonyl chloride was added, followed by dropwise addition of 10 ml. of triethylamine. A mildly exothermic reaction took place, after which stirring of the mixture was continued at room temperature overnight. The mixture was then washed with 1N hydrochloric acid and water and dried over anhydrous sodium carbonate. On evaporation to dryness, crude 3-(cyclopropylcarbonyl)-1,2,3,4,8,9-hexahydropyrido[4',3':2,3]indolo[1,7-ab][1]benzazepine was obtained as a glassy product. Recrystallization from ethanol yielded the pure material, m.p. 154°-156° C.

Workup

  1. additionfollowed by dropwise addition of 10 ml
  2. customA mildly exothermic reaction
  3. washThe mixture was then washed with 1N hydrochloric acid and water
  4. dry with materialdried over anhydrous sodium carbonate
  5. customOn evaporation to dryness

Sources & evidence

ORD record
ord-75f48ae26de445fc93ebe9fb80d13cb3
Source dataset
uspto-grants-1977_04
Patent number
US04018930

Reaction notes

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