Trifluoroacetic acid → 4-[5-(4-Chlorophenyl)-4-(2,2,2-trifluoroethoxymethyl)-oxazol-2-yl]piperidine trifluoroacetate

HRID 2288978Notes

Reaction equation

HRID 2288978 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[O:18][C:19]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)=[C:20]([CH2:22][O:23][CH2:24][C:25]([F:28])([F:27])[F:26])[N:21]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39]>>[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39].[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([C:19]2[O:18][C:17]([CH:14]3[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]3)=[N:21][C:20]=2[CH2:22][O:23][CH2:24][C:25]([F:26])([F:27])[F:28])=[CH:30][CH:31]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 542750074-[5-(4-Chlorophenyl)-4-(2,2,2-trifluoroethoxymethyl)-oxazol-2-yl]-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 187004174-[5-(4-Chlorophenyl)-4-(2,2,2-trifluoroethoxymethyl)-oxazol-2-yl]piperidine trifluoroacetate

Procedure

A solution of 4-[5-(4-Chlorophenyl)-4-(2,2,2-trifluoroethoxymethyl)-oxazol-2-yl]-piperidine-1-carboxylic acid benzyl ester (3.7600 g, 7.3880 mmol) in trifluoroacetic acid (10 mL, 130 mmol) was stirred at RT for 3 d, then concentrated to a thick oil. This is dissolved with heating in a mixture of hexane and diethyl ether which, upon cooling, precipitated cream-colored solids. These are collected, washed with hexane and dried in vacuo at RT. Reworking the mother liquors gives a second crop of solids. The crops are combined to give the title compound as cream colored solids.

Workup

  1. concentrationconcentrated to a thick oil
  2. dissolutionThis is dissolved
  3. temperaturewith heating in a mixture of hexane and diethyl ether which
  4. temperatureupon cooling
  5. customprecipitated cream-colored solids
  6. customThese are collected
  7. washwashed with hexane
  8. customdried in vacuo at RT
  9. customReworking the mother liquors gives a second crop of solids

Sources & evidence

ORD record
ord-c125f9eca7e64dc6823e77fdf11cba8b
Source dataset
uspto-grants-2000_07
Patent number
US06090825

Reaction notes

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