Ammonia → 6-Hydroxy-2-(4-(4-phenylbenzoylamino)butyl)-1,2,3,4-tetrahydroisoquinoline

HRID 650562Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:31])[C:19]1[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:21][CH:20]=1)[CH2:7][CH2:6]2.B(Br)(Br)Br.N>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:31])[C:19]1[CH:20]=[CH:21][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:23][CH:24]=1)[CH2:7][CH2:6]2

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 6-methoxy-2-(4-(4-phenylbenzoylamino)butyl)-1,2,3,4-tetrahydroisoquinoline (1.18 g, 2.8 mmol) and dichloromethane (50 ml) was treated dropwise with a solution of boron tribromide in dichloromethane (1M; 8.4 ml). The mixture was stirred at 20° C. for 18 h, then poured into a mixture of ice (100 g) and 0.880 ammonia (100 ml). Resulting mixture was extracted with dichloromethane (3×50 ml) and the combined extracts were dried (Na2SO4) and evaporated in vacuo. The residue was triturated with ether to give the title compound (0.86 g, 77%) as a yellow solid.

Workup

customResulting mixture
extractionwas extracted with dichloromethane (3×50 ml)
dry with materialthe combined extracts were dried (Na2SO4)
customevaporated in vacuo
customThe residue was triturated with ether

Sources & evidence

ORD record: ord-6d033ac651854fce8133b84442aa183b
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06274593B1

Reaction notes

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