Trifluoroacetic acid → (S)-1'-[3-(3,4-dichloro-phenyl)-4-methylamino-butyl]-[1,4']bipiperidinyl-2-one

HRID 2221073Notes

Reaction equation

HRID 2221073 reaction equation
FC(F)(F)C(O)=O.C(O[C:13](=O)[N:14]([CH2:16][C@H:17]([C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([Cl:40])[CH:34]=1)[CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][CH:23]([N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][C:27]2=[O:32])[CH2:22][CH2:21]1)C)(C)(C)C>ClCCl.[OH-].[Na+]>[Cl:40][C:35]1[CH:34]=[C:33]([C@@H:17]([CH2:16][NH:14][CH3:13])[CH2:18][CH2:19][N:20]2[CH2:21][CH2:22][CH:23]([N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][C:27]3=[O:32])[CH2:24][CH2:25]2)[CH:38]=[CH:37][C:36]=1[Cl:39]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 69224867(S)-[2-(3,4-Dichloro-phenyl)-4-(2-oxo-[1,4']bipiperidinyl-1'-yl)-butyl]-methyl-carbamic acid tert-butyl ester

Product 1

HCID 69222215(S)-1'-[3-(3,4-dichloro-phenyl)-4-methylamino-butyl]-[1,4']bipiperidinyl-2-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

Trifluoroacetic acid (13.1 mL) was added to a solution of (S)-[2-(3,4-dichloro-phenyl)-4-(2-oxo-[1,4′]bipiperidinyl-1′-yl)-butyl]-methyl-carbamic acid tert-butyl ester (8.73 g) in dichloromethane (300 mL). After stirring for 30 minutes additional trifluoroacetic acid (13.1 mL) was added. After 1.5 hours the reaction was diluted with aqueous sodium hydroxide, and the layers were separated. The organic layer was washed with water, dried and evacuated to a viscous oil which was not purified further. MS: m/z=412(M+1).

Workup

  1. additionwas added
  2. customthe layers were separated
  3. washThe organic layer was washed with water
  4. customdried
  5. customevacuated to a viscous oil which
  6. customwas not purified further

Sources & evidence

ORD record
ord-b7468632f8e049159082dcea7ea0199f
Source dataset
uspto-grants-2008_05
Patent number
US07368461B2

Reaction notes

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