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Isobutylene oxide → N-Cyclopropyl-N-[1-(2-hydroxy-2-methyl-propyl)-piperidin-4-yl]-4-oxazol-5-yl-benzamide

HRID 1424524
Notes
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Reaction equation

HRID 1424524 reaction equation
[CH3:1][C:2]1([CH3:5])[O:4][CH2:3]1.[CH:6]1([N:9]([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[C:10](=[O:22])[C:11]2[CH:16]=[CH:15][C:14]([C:17]3[O:21][CH:20]=[N:19][CH:18]=3)=[CH:13][CH:12]=2)[CH2:8][CH2:7]1>CO.O>[CH:6]1([N:9]([CH:23]2[CH2:28][CH2:27][N:26]([CH2:3][C:2]([OH:4])([CH3:5])[CH3:1])[CH2:25][CH2:24]2)[C:10](=[O:22])[C:11]2[CH:12]=[CH:13][C:14]([C:17]3[O:21][CH:20]=[N:19][CH:18]=3)=[CH:15][CH:16]=2)[CH2:8][CH2:7]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 11208Isobutylene oxide2×HCID 68289931N-Cyclopropyl-4-oxazol-5-yl-N-piperidin-4-yl-benzamide

Product 1

HCID 86709612N-Cyclopropyl-N-[1-(2-hydroxy-2-methyl-propyl)-piperidin-4-yl]-4-oxazol-5-yl-benzamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

1,1-Dimethyloxirane (88 μL) is added to N-cyclopropyl-4-oxazol-5-yl-N-piperidin-4-yl-benzamide (100 mg) in methanol (5 mL). The mixture is stirred for 4 h at room temperature and at 50° C. over night. Since the conversion is still incomplete, another portion of 1,1-dimethyloxirane (88 μL) is added and the mixture is stirred for 8 h at 50° C. The reaction mixture is diluted with water (10 mL) and stirred for 1 h at room temperature. The precipitate is filtered off and washed with water and t-butyl methylether to give the title compound. LC (method 2): tR=1.00 min; Mass spectrum (ESI+): m/z=384 [M+H]+.

Workup

  1. stirringthe mixture is stirred for 8 h at 50° C
  2. stirringstirred for 1 h at room temperature
  3. filtrationThe precipitate is filtered off
  4. washwashed with water and t-butyl methylether

Sources & evidence

ORD record
ord-ce4b9c89f8444f60b8eca181ed5f6a37
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08927726B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes