Formaldehyde → HCID 23624253, compound

HRID 1436996Notes

Reaction equation

HRID 1436996 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]3[CH2:16][CH2:15][NH:14][CH2:13][C:12]4[CH:17]=[CH:18][CH:19]=[CH:20][C:11]3=4)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C=O.[C:23](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]3[CH2:16][CH2:15][N:14]([CH3:23])[CH2:13][C:12]4[CH:17]=[CH:18][CH:19]=[CH:20][C:11]3=4)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 23624258HCID 23624258, compound

Product 1

HCID 23624253HCID 23624253, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

5-(1H-indol-5-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepine was subjected to reductive amination using formaldehyde and sodium triacetoxyborohydride in 1,2-dichloroethane to give 5-(1H-indol-5-yl)-2-methyl-2,3,4,5-tetrahydro-1H-benzo[c]azepine as a white powder in 50% yield.

Sources & evidence

ORD record
ord-44d21bdfcd5e4604817933cdc3fc9f77
Source dataset
uspto-grants-2009_11
Patent number
US07622462B2

Reaction notes

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