Ammonia → trans-8-Chloro-2-methyl-1,2,3,3a,4,5-hexahydrobenzo[e]pyrrolo[3,4-c]azepin-6(10bh)-one

HRID 84934Notes

Reaction equation

HRID 84934 reaction equation
N.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:13]2[C@H:17]([C:18]#[N:19])[CH2:16][N:15]([CH3:20])[CH2:14]2)=[C:7]([CH:12]=1)[C:8](OC)=[O:9]>CO.[Ni]>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[C@@H:13]3[CH2:14][N:15]([CH3:20])[CH2:16][C@H:17]3[CH2:18][NH:19][C:8](=[O:9])[C:7]=2[CH:12]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 131731902HCID 131731902, compound

Product 1

HCID 54673810trans-8-Chloro-2-methyl-1,2,3,3a,4,5-hexahydrobenzo[e]pyrrolo[3,4-c]azepin-6(10bh)-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a 2 gallon Parr vessel was charged Raney®-nickel (77 g, Grace 2800 (water decanted)) and 7 M ammonia in methanol (3 L) and trans-methyl 5-chloro-2-(4-cyano-1-methylpyrrolidin-3-yl)benzoate (152.7 g). The reactor was sealed, purged with nitrogen, then purged with hydrogen and pressurized to 30 psi with hydrogen. After 2 hours, the reaction mixture was filtered through a polypropylene cartridge and rinsed with methanol (1 L). The solvent was removed under vacuum to provide the title compound (crude) used as is in Example 199.

Workup

  1. customThe reactor was sealed
  2. custompurged with nitrogen
  3. custompurged with hydrogen
  4. filtrationthe reaction mixture was filtered through a polypropylene cartridge
  5. washrinsed with methanol (1 L)
  6. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-d9c96805d7ba4ad5b5b38ec182eed7ac
Source dataset
uspto-grants-2014_09
Patent number
US08846951B2

Reaction notes

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