Benzyl Bromide → Acetyl 9-benzyl-1,2,3,4-tetrahydro-beta-carboline

Reaction equation

[C:1]([CH:4]1[C:16]2[NH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH2:7][CH2:6][NH:5]1)(=[O:3])[CH3:2].[H-].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[C:1]([CH:4]1[C:16]2[N:15]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH2:7][CH2:6][NH:5]1)(=[O:3])[CH3:2]

Participants

Procedure

2 acetyl-9 benzyl-1,2,3,4-tetrahydro-β-carboline was prepared as follows: Under a nitrogen atmosphere, 8.0 mmol of 2 acetyl-1,2,3,4-tetrahydro-β-carboline (1.71 was dissolved in 4Q mL dry dimethylformamide (DMF). The solution was stirred over ice, and NaH (2 g) was added under N2. The suspension was stirred for 1 hour, and then benzylbromide (9.2 mmol, 1.56 was slowly to the cooled suspension. After a further 2 hours of stirring at ambient temperature, the mixture was filtered and the filtrate added to 320 mL 0.1 N HCl. Crude 2-acetyl- 9-benzyl-1,2,3,4-tetrahydro-β-carboline separated as an oil. The oil was collected by centrifugation, washed with water, and dried over anhydrous MgSO:. The product was purified by standard chromatographic procedures using a 60:40 mixture of ether:hexane.