Dimethylamine → HCID 70009678, compound

HRID 1266026Notes

Reaction equation

HRID 1266026 reaction equation
[O:1]=[C:2]1[N:13]2[C:14]3[C:10]([CH:11]=[CH:12]2)=[CH:9][C:8]([C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=2)[CH:18]=O)=[CH:7][C:6]=3[CH2:5][NH:4][CH2:3]1.[CH3:23][NH:24][CH3:25]>O>[CH3:23][N:24]([CH2:18][C:17]1[CH:16]=[C:15]([C:8]2[CH:9]=[C:10]3[C:14]4=[C:6]([CH2:5][NH:4][CH2:3][C:2](=[O:1])[N:13]4[CH:12]=[CH:11]3)[CH:7]=2)[CH:22]=[CH:21][CH:20]=1)[CH3:25]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 86758920HCID 86758920, compound

Product 1

HCID 70009678HCID 70009678, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using the reductive amination procedure described in Example 82, the title compound was synthesized from 3-(1-oxo-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-6-yl)-benzaldehyde and dimethylamine in 87% yield as a white solid: mp 98-100° C.; 1H NMR (DMSO-d6) δ 2.18 (s, 6H), 3.47 (br s, 4H), 4.30-4.32 (m, 2H), 6.70 (s, 1H), 7.17 (t, 1H, J=6.0 Hz), 7.35-7.37 (m, 1H), 7.43-7.50 (m, 3H), 7.78 (d, 1H, J=6.0 Hz), 7.81 (d, 1H, J=6.0 Hz), 8.38 (t, 1H, J=6.0 Hz). HRMS calcd. for C20H21N3O 319.1685 (M+), found 319.1682. Anal. (C20H21N3O.0.25 H2O) C, H, N.

Sources & evidence

ORD record
ord-0b53262413b14b1f84eb93e32c4109f9
Source dataset
uspto-grants-2003_04
Patent number
US06548494B1

Reaction notes

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