(r)-3-Cyclohexyl-2,3-dihydro-6-[(cis)-4-benzyl-2,6-dimethylpiperazin-1-yl-carbonyl]pyrrolo[1,2,3-de]-1,4-benzoxazine hydrochloride salt → (r)-3-Cyclohexyl-2,3-dihydro-6-[(cis)-2,6-dimethylpiperazin-1-ylcarbonyl]pyrrolo-[1,2,3-de]-1,4-benzoxazine hydrochloride salt

HRID 500449Notes

Reaction equation

HRID 500449 reaction equation
[ClH:1].[CH:2]1([C@H:8]2[N:13]3[CH:14]=[C:15]([C:20]([N:22]4[C@H:27]([CH3:28])[CH2:26][N:25](CC5C=CC=CC=5)[CH2:24][C@@H:23]4[CH3:36])=[O:21])[C:16]4[CH:17]=[CH:18][CH:19]=[C:11]([C:12]=43)[O:10][CH2:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1>C(O)C.[Pd]>[ClH:1].[CH:2]1([C@H:8]2[N:13]3[CH:14]=[C:15]([C:20]([N:22]4[C@H:23]([CH3:36])[CH2:24][NH:25][CH2:26][C@@H:27]4[CH3:28])=[O:21])[C:16]4[CH:17]=[CH:18][CH:19]=[C:11]([C:12]=43)[O:10][CH2:9]2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 68674127(r)-3-Cyclohexyl-2,3-dihydro-6-[(cis)-4-benzyl-2,6-dimethylpiperazin-1-yl-carbonyl]pyrrolo[1,2,3-de]-1,4-benzoxazine hydrochloride salt

Product 1

HCID 68674616(r)-3-Cyclohexyl-2,3-dihydro-6-[(cis)-2,6-dimethylpiperazin-1-ylcarbonyl]pyrrolo-[1,2,3-de]-1,4-benzoxazine hydrochloride saltYield 61.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (R)-3-cyclohexyl-2,3-dihydro-6-[(cis)-4-benzyl-2,6-dimethylpiperazin-1-ylcarbonyl]pyrrolo[1,2,3-de]-1,4-benzoxazine hydrochloride salt (200 mg, 0.42 mmol) in ethanol (5 ml) was added 10% palladium on charcoal (10 mg). The mixture was stirred under a hydrogen atmosphere for 16 h at room temperature. The mixture was filtered and the solvent removed in vacuo to afford the title compound as a white solid (100 mg, 0.26 mmol).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-35850f477d9046608fc48c2c18152818
Source dataset
uspto-grants-2010_08
Patent number
US07772227B2

Reaction notes

Loading…