Methylamine → HCID 70008663, compound

HRID 1266027Notes

Reaction equation

HRID 1266027 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][NH2:24]>O>[CH3:23][NH: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

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86758920HCID 86758920, compound

Product 1

HCID 70008663HCID 70008663, compoundYield 94%

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 methylamine in 94% yield as a pale-yellow solid: mp 128-130° C.; 1H NMR (DMSO-d6) δ 2.29 (s, 3H), 3.48 (br s, 2H), 3.71 (s, 2H), 4.30-4.33 (m, 2H), 6.69 (s, 1H), 7.17 (t, 1H, J=9.0 Hz), 7.38-7.39 (m, 1H), 7.44-7.46 (m, 2H), 7.54 (s, 1H), 7.80 (t, 2H, J=9.0 Hz), 8.39 (t, 1H, J=6.0 Hz). HRMS calcd. for C19H19N3O 305.3828 (M+), found 305.1520. Anal. (C19H19N3O.0.6 H2O) C, H, N.

Sources & evidence

ORD record
ord-e3e446249508419287f46526aadacb15
Source dataset
uspto-grants-2003_04
Patent number
US06548494B1

Reaction notes

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