N-trityl-2-[4-(benzoxazol-2-yl)benzyloxy]ethylamine → 2-[4-(Benzoxazol-2-yl)benzyloxy]ethylamine hydrochloride

HRID 863838Notes

Reaction equation

C([NH:20][CH2:21][CH2:22][O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[O:32][C:33]3[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=3[N:35]=2)=[CH:27][CH:26]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[ClH:40].CCO>CCO>[ClH:40].[O:32]1[C:33]2[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=2[N:35]=[C:31]1[C:28]1[CH:29]=[CH:30][C:25]([CH2:24][O:23][CH2:22][CH2:21][NH2:20])=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 80 °C

Procedure

N-trityl-2-[4-(benzoxazol-2-yl)benzyloxy]ethylamine (9.1 g; 17.8 mmol) is suspended in EtOH and treated with HCl/EtOH until acidic by pH paper. The reaction mixture is heated at 80° C. for 3 hours keeping the reaction acidic. The reaction mixture is then cooled and the solid is filtered and washed with EtOH to give 2-[4-(benzoxazol-2-yl)benzyloxy]ethylamine hydrochloride (m.p. 232°-233° C.) as a white solid which is used directly in Step F.

Workup

temperatureThe reaction mixture is then cooled
filtrationthe solid is filtered
washwashed with EtOH

Sources & evidence

ORD record: ord-5f590f4aa6e3495ba5fd5bf209096803
Source dataset: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05561143

Reaction notes

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