HCID 22455949, compound → HCID 22455946, compound

HRID 2185962Notes

Reaction equation

HRID 2185962 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=2)([OH:14])[CH2:9]1)=O)(C)(C)C>C(OCC)(=O)C>[ClH:21].[Cl:22][C:17]1[CH:16]=[C:15]([C:10]2([OH:14])[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]2)[CH:20]=[CH:19][C:18]=1[Cl:21]

Participants

3

Reactant 1

HCID 22455949HCID 22455949, compound

Product 1

HCID 22455946HCID 22455946, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

Through a solution of N-t-butoxycarbonyl-3-(3,4-dichlorophenyl)-3-hydroxy piperidine (150 mg, 0.44 mmol) in ethyl acetate (5 ml) cooled to 0° C. is bubbled HCl (g) for 5 min. The reaction mixture is stirred at 25° C. until reaction completion. The reaction mixture is concentrated in vacuo and flushed with ethyl acetate/concentrated 3 times to provide 3-(3,4-dichlorophenyl)-3-hydroxy piperidine hydrochloride which is converted without further purification to 3-(3,4-dichlorophenyl)-3-hydroxy piperidine-1-carboxylic acid {4-[(2,2-dimethyl-propionylamino)-methyl]-phenyl}-amide using N-(4-isocyanato-benzyl)-2,2-dimethyl-propionamide as described in example 1a.

Workup

  1. customis bubbled HCl (g) for 5 min
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. customflushed with ethyl acetate/
  4. concentrationconcentrated 3 times

Sources & evidence

ORD record
ord-3e8be0888cb64a9ab1b50136e21da24a
Source dataset
uspto-grants-2002_06
Patent number
US06403612B2

Reaction notes

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