Allyl bromide → HCID 12837724, compound

HRID 1447403Notes

Reaction equation

HRID 1447403 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.[CH2:19](Br)[CH:20]=[CH2:21]>CN(C)C=O.C(N(CC)CC)C.C(OCC)C>[CH2:21]([N:2]1[CH2:3][CH2:4][N:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[CH2:9][N:8]3[CH:16]=[CH:17][CH:18]=[C:7]3[CH:6]2[CH2:1]1)[CH:20]=[CH2:19]

Participants

6

Reactant 2

HCID 7841Allyl bromideHCID 12837720HCID 12837720, compound

Product 1

HCID 12837724HCID 12837724, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To the solution of 4.8 g of 1,3,4,14b-tetrahydro-2H,10H-pyrazino[1,2-a]pyrrolo[2,1-c][1,4]-benzodiazepine in 20 ml of dimethyl formamide and 2.44 g of triethylamine, 2.91 g of allyl bromide are added dropwise while stirring. After one hour, the mixture is diluted with diethyl ether, washed with water and saturated aqueous sodium chloride and the aqueous phase is once more extracted with diethyl ether. The combined organic solutions are washed with saturated aqueous sodium bicarbonate, dried, evaporated and the residue triturated with diethyl ether, to yield the 2-allyl-1,3,4,14b-tetrahydro-10H--pyrazino[1,2-a]pyrrolo[2,1-c][1,4]-benzodiazepine melting at 130°-132°.

Workup

  1. washwashed with water and saturated aqueous sodium chloride
  2. extractionthe aqueous phase is once more extracted with diethyl ether
  3. washThe combined organic solutions are washed with saturated aqueous sodium bicarbonate
  4. customdried
  5. customevaporated
  6. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-e55f1d5ad3e44a088158210febfe449b
Source dataset
uspto-grants-1982_02
Patent number
US04316900

Reaction notes

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