Allyl bromide → HCID 12837724, compound

HRID 1902194Notes

Reaction equation

HRID 1902194 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 dimethylformamide 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-046d07d1d0864928b10dbfa3f32b23ea
Source dataset
uspto-grants-1982_12
Patent number
US04362666

Reaction notes

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