Methyl iodide → 1-(3-{4-[3-(3,4-Dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-propyl)-1-methyl-piperidinium iodide

HRID 1867423Notes

Reaction equation

HRID 1867423 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([N:13]2[CH2:19][CH2:18][C:17](=[O:20])[N:16]([CH2:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[I:30][CH3:31]>CO>[I-:30].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]([N:13]2[CH2:19][CH2:18][C:17](=[O:20])[N:16]([CH2:21][CH2:22][CH2:23][N+:24]3([CH3:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 684319841-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-4-(3-piperidin-1-yl-propyl)-[1,4]diazepan-5-one

Product 1

HCID 684328011-(3-{4-[3-(3,4-Dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-propyl)-1-methyl-piperidinium iodideYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-4-(3-piperidin-1-yl-propyl)-[1,4]diazepan-5-one (example 4) (27 mg, 62 umol) in MeOH (0.5 ml) was added iodomethane (40 uL, 620 umol) and the reaction left for overnight at room temperature. Concentration of the mixture affording the title product (35 mg, 98%) as a white solid. MS: 452.2 (M+, 2Cl).

Sources & evidence

ORD record
ord-e70e4a9c5a8447be99150f3d82015281
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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