HCID 86583958, compound → 2,2,2-Trifluoro-1-[4-(6-methoxy-3,4-dihydro-isoquinolin-1-yl)-piperidin-1-yl]-ethanone

HRID 397061Notes

Reaction equation

HRID 397061 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11][C:12]([CH:14]2[CH2:19][CH2:18][N:17]([C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])[CH2:16][CH2:15]2)=O)[CH:6]=[CH:7][CH:8]=1>O=P(Cl)(Cl)Cl>[F:22][C:21]([F:24])([F:23])[C:20]([N:17]1[CH2:18][CH2:19][CH:14]([C:12]2[C:6]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[CH2:9][CH2:10][N:11]=2)[CH2:15][CH2:16]1)=[O:25]

Participants

3

Reactant 1

HCID 86583958HCID 86583958, compound

Product 1

HCID 181723932,2,2-Trifluoro-1-[4-(6-methoxy-3,4-dihydro-isoquinolin-1-yl)-piperidin-1-yl]-ethanoneYield 88.3%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A stirred solution of 1-trifluoroacetyl-piperidine-4-carboxylic acid [2-(3-methoxy-phenyl)-ethyl]-amide (1.04 g, 2.9 mmol) in POCl3 under an atmosphere of N2 was heated at reflux for 2.5 hours. The reaction was allowed to cool to RT and the POCl3 was removed in vacuo. The residual oil was suspended in toluene (20 ml) and concentrated in vacuo (this process was repeated twice more), leaving the desired product as a tan colored solid (0.872 g, 2.56 mmol, 88% yield). MS 341 (M+1)

Workup

  1. temperatureat reflux for 2.5 hours
  2. customthe POCl3 was removed in vacuo
  3. concentrationconcentrated in vacuo (this process

Sources & evidence

ORD record
ord-e2ab688b7a3f4015909250ff6dcb8c4d
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

Loading…