Hydrochloric Acid → 1-((R)-(3-chlorophenyl)((R)-piperidin-3-yl)methoxy)propan-2-one

HRID 451917Notes

Reaction equation

HRID 451917 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([O:22][CH2:23][C:24](OC)([O:26]C)[CH3:25])[C@@H:9]2[CH2:14][CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)[CH:5]=[CH:6][CH:7]=1.Cl>CC#N>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([C@@H:9]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]2)[O:22][CH2:23][C:24](=[O:26])[CH3:25])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59201517(R)-tert-butyl 3-((R)-(3-chlorophenyl)(2,2-dimethoxypropoxy)methyl)piperidine-1-carboxylate

Product 1

HCID 592017501-((R)-(3-chlorophenyl)((R)-piperidin-3-yl)methoxy)propan-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (R)-tert-butyl 3-((R)-(3-chlorophenyl)(2,2-dimethoxypropoxy)methyl)piperidine-1-carboxylate, obtained as described above, 2 N HCl (100 mL) and CH3CN (100 mL) was vigorously stirred at rt for 22 h. After the reaction mixture was evaporated under reduced pressure, the crude 1-((R)-(3-chlorophenyl)((R)-piperidin-3-yl)methoxy)propan-2-one was directly used in the next step without further purification. MS ESI +ve m/z 284 (M+H).

Workup

  1. customobtained
  2. customAfter the reaction mixture was evaporated under reduced pressure
  3. customthe crude 1-((R)-(3-chlorophenyl)((R)-piperidin-3-yl)methoxy)propan-2-one was directly used in the next step without further purification

Sources & evidence

ORD record
ord-71c68b791c144236a6ddf9f04f1e7760
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

Loading…