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

HRID 650561Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7][CH2:6]2.[C:13]1([C:19]2[CH:32]=[CH:31][C:22]([C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH:29]=O)=[O:24])=[CH:21][CH:20]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([CH2:29][CH2:28][CH2:27][CH2:26][NH:25][C:23](=[O:24])[C:22]1[CH:31]=[CH:32][C:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:20][CH:21]=1)[CH2:7][CH2:6]2

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 6-methoxy-1,2,3,4-tetrahydroisoquinoline (1.00 g, 6.2 mmol), 4-(4-phenylbenzoylamino)butyraldehyde (1.64 g, 6.2 mmol), sodium triacetoxyborohydride (1.94 g, 9.2 mmol) and dichloromethane (50 ml) was stirred at 20° C. for 18 h. Resulting solution was partitioned between saturated aqueous NAHCO3 (50 ml) and dichloromethane (3×50 ml). Combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give a solid. Trituration with 1:1 dichloromethane-ether gave the title compound (0.80 g, 32%).

Workup

customResulting solution was partitioned between saturated aqueous NAHCO3 (50 ml) and dichloromethane (3×50 ml)
dry with materialCombined organic extracts were dried (Na2SO4)
customevaporated in vacuo
customto give a solid

Sources & evidence

ORD record: ord-1fc5afc881e24cf9bf2b3d2b2a23ae96
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06274593B1

Reaction notes

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