4-Vinylpyridine → N-[1-[2-(4-pyridinyl)ethyl]-4-piperidinyl]-2-benzoxazolamine

HRID 1085693

Reaction equation

HRID 1085693 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)=[CH2:2].[NH:9]1[CH2:14][CH2:13][CH:12]([NH:15][C:16]2[O:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)[CH2:11][CH2:10]1>C(O)CCC>[N:6]1[CH:7]=[CH:8][C:3]([CH2:1][CH2:2][N:9]2[CH2:10][CH2:11][CH:12]([NH:15][C:16]3[O:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)[CH2:13][CH2:14]2)=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 75024-VinylpyridineHCID 14575294N-(4-piperidinyl)-2-benzoxazolamine

Product 1

HCID 14575870N-[1-[2-(4-pyridinyl)ethyl]-4-piperidinyl]-2-benzoxazolamineYield 62%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 3.2 parts of 4-(1-ethenyl)pyridine, 2.1 parts of N-(4-piperidinyl)-2-benzoxazolamine and 80 parts of 1-butanol was stirred and refluxed for 48 hours. The reaction mixture was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (97:3 by volume) saturated with ammonia, as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2,2'-oxybispropane, yielding 2 parts (62%) of N-[1-[2-(4-pyridinyl)ethyl]-4-piperidinyl]-2-benzoxazolamine; mp. 146.9° C. (450).

Workup

  1. temperaturerefluxed for 48 hours
  2. customThe reaction mixture was evaporated
  3. customThe residue was purified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (97:3 by volume) saturated with ammonia
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. customThe residue was crystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-6f9201b8286849fbbca0c9ac6be90757
Source dataset
uspto-grants-1991_04
Patent number
US05010198

Linked notes

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