p-Chlorophenacyl bromide → HCID 12837734, compound

HRID 1447406Notes

Reaction equation

HRID 1447406 reaction equation
[CH2:1]1[CH:6]2[C:7]3[N:8]([CH:16]=[CH:17][CH:18]=3)[CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:5]2[CH2:4][CH2:3][NH:2]1.Br[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)=[O:22]>CN(C)C=O.C(N(CC)CC)C.C(OCC)C>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([C:21]([CH2:20][N:2]2[CH2:3][CH2:4][N:5]3[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[CH2:9][N:8]4[CH:16]=[CH:17][CH:18]=[C:7]4[CH:6]3[CH2:1]2)=[O:22])=[CH:24][CH:25]=1

Participants

6

Reactant 2

HCID 68303p-Chlorophenacyl bromideHCID 12837720HCID 12837720, compound

Product 1

HCID 12837734HCID 12837734, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To the solution of 500 mg of 1,3,4,14b-tetrahydro-2H,10H-pyrazino[1,2-a]pyrrolo[2,1-c][1,4]benzodiazepine in 7.5 ml of dimethylformamide and 350 mg of triethylamine, 470 mg of α-bromo-p-chloroacetophenone are added and the mixture is stirred at room temperature for 2 hours. It is diluted with 60 ml of diethyl ether, washed with water, dried and evaporated. The residue is taken up in 15 ml of chloroform and the solution again evaporated, to yield the 2-(p-chlorobenzoylmethyl)-1,3,4,14b-tetrahydro-10H-pyrazino[1,2-a]pyrrolo[2,1-c][1,4]benzodiazepine melting at 71°-74°.

Workup

  1. washwashed with water
  2. customdried
  3. customevaporated
  4. customthe solution again evaporated

Sources & evidence

ORD record
ord-5263085dac424a4eaf21d583e073b24b
Source dataset
uspto-grants-1982_02
Patent number
US04316900

Reaction notes

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