N,N-Diethyl 4-bromo-2-chlorobenzamide → (R)-1,3,4,10b-tetrahydro-7-chloro-9-hydroxy-pyrazino[2,1-a]isoindol-6(2H)-one Hydrochloric Acid

HRID 1159067Notes

Reaction equation

HRID 1159067 reaction equation
C(N(CC)C(=O)C1C=CC(Br)=CC=1[Cl:12])C.C(N(CC)C(=O)C1C=CC(Br)=CC=1OC(F)(F)F)C.C(OC([N:42]1[CH2:62][CH2:61][N:45]2[C:46](=[O:60])[C:47]3[C:52]([CH:44]2[CH2:43]1)=[CH:51][C:50]([O:53]C)=[CH:49][C:48]=3OC(F)(F)F)=O)(C)(C)C>>[ClH:12].[Cl:12][C:48]1[CH:49]=[C:50]([OH:53])[CH:51]=[C:52]2[C:47]=1[C:46](=[O:60])[N:45]1[CH2:61][CH2:62][NH:42][CH2:43][C@H:44]12

Participants

4

Reactant 3

HCID 16115931N,N-Diethyl 4-bromo-2-chlorobenzamideHCID 686878354-bromo-N,N-diethyl-2-(trifluoromethoxy)benzamideHCID 68687866N-(t-butoxycarbonyl)-(+/-)-1,3,4,10b-tetrahydro-9-methoxy-7-trifluoromethoxy-pyrazino[2,1-a]isoindol-6(2H)-one

Product 1

HCID 11242816(R)-1,3,4,10b-tetrahydro-7-chloro-9-hydroxy-pyrazino[2,1-a]isoindol-6(2H)-one Hydrochloric Acid

Procedure

Prepared according to procedures described in Example 128 Step A with substitution of N-(t-butoxycarbonyl)-(R)-1,3,4,10b-tetrahydro-7-chloro-9-methoxy-pyrazino[2,1-a]isoindol-6(2H)-one, produced by procedures described in Example 126 with the substitution of N,N-diethyl-4-bromo-2-chlorobenzamide for N,N-diethyl-4-bromo-2-trifluoromethoxybenzamide, for N-(t-butoxycarbonyl)-(±)-1,3,4,10b-tetrahydro-9-methoxy-7-trifluoromethoxy-pyrazino[2,1-a] isoindol-6(2H)-one. Followed by the separation of enantiomers according to the procedures described in Example 128 Step D. MS (ESI) 239 (M−Cl).

Workup

  1. customPrepared
  2. customproduced by procedures
  3. customFollowed by the separation of enantiomers

Sources & evidence

ORD record
ord-7fe5faad8de94114bb731f4cc9a39b93
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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