Azanium;hydrate → 2-(4-(Piperazin-1-ylmethyl)phenyl)benzo[d]oxazole-7-carboxamide

HRID 415212Notes

Reaction equation

HRID 415212 reaction equation
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[O:15][C:16]4[C:22]([C:23]([O:25]C)=O)=[CH:21][CH:20]=[CH:19][C:17]=4[N:18]=3)=[CH:10][CH:9]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.O.[NH4+:28]>>[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[O:15][C:16]4[C:22]([C:23]([NH2:28])=[O:25])=[CH:21][CH:20]=[CH:19][C:17]=4[N:18]=3)=[CH:10][CH:9]=2)[CH2:2][CH2:3][NH:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 22024077Azanium;hydrateHCID 66621147Methyl 2-(4-(piperazin-1-ylmethyl)phenyl)benzo[d]oxazole-7-carboxylate

Product 1

HCID 666208362-(4-(Piperazin-1-ylmethyl)phenyl)benzo[d]oxazole-7-carboxamideYield 33%

Procedure

Methyl 2-(4-(piperazin-1-ylmethyl)phenyl)benzo[d]oxazole-7-carboxylate in ammonium water (10 mL) was stirred at 30° C. for 17 hr, cooled, and filtered; then the cake was washed with water, dried under reduced pressure to obtain 2-(4-(piperazin-1-ylmethyl)phenyl)benzo[d]oxazole-7-carboxamide as a white solid (80 mg, yield 33% for two steps). 1H NMR (400 MHz, DMSO-d6) δ 2.32 (s, 4H), 2.69-2.72 (t, J=4 Hz, 4H), 3.53 (s, 2H), 3.98 (s, 1H), 7.45-7.49 (t, J=8 Hz, 1H), 7.54-7.56 (d, J=8 Hz, 2H), 7.79-7.80 (d, J=7.2 Hz, 1H), 7.86-7.89 (d, J=10.4 Hz, 2H), 7.93-7.95 (d, J=8 Hz, 1H), 8.23-8.25 (d, J=8 Hz, 2H); LC-MS (ESI) m/z 337 [M+1]+.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. washthen the cake was washed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-c9415c2951b04d84aea4f8c650a88230
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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