Piperidine → HCID 68433229, compound

HRID 1867454Notes

Reaction equation

HRID 1867454 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[C:5]([CH2:7][N:8]1[C:14](=[O:15])[CH2:13][CH2:12][N:11]([C:16](=[O:27])/[CH:17]=[CH:18]/[C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)[CH2:10][CH2:9]1)=[CH2:6])[CH3:2].[NH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:28])[CH:5]([CH2:6][N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[CH2:7][N:8]1[C:14](=[O:15])[CH2:13][CH2:12][N:11]([C:16](=[O:27])/[CH:17]=[CH:18]/[C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)[CH2:10][CH2:9]1)[CH3:2]

Participants

5

Reactant 3

HCID 8082Piperidine2×HCID 10796Cesium carbonateHCID 684348702-{4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-ylmethyl}-acrylic acid ethyl ester

Product 1

HCID 68433229HCID 68433229, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 0.80 g (1.88 mmol) of 2-{4-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-ylmethyl}-acrylic acid ethyl ester, 0.56 ml (5.64 mmol) of piperidine and 1.83 g (5.61 mmol) of cesium carbonate in 32 ml of acetonitrile was stirred over night at RT. Additional 0.37 ml (3.76 mmol) of piperidine were added and after 1 h, cesium carbonate was filtrated and the solvent evaporated. Purification by flash silica gel column (CH2Cl2/MeOH 98:2 to 96:4) gave 0.43 g (44%) of the title compound as colorless foam. MS: 510.4 (MH+, 2Cl).

Workup

  1. filtrationcesium carbonate was filtrated
  2. customthe solvent evaporated
  3. customPurification by flash silica gel column (CH2Cl2/MeOH 98:2 to 96:4)

Sources & evidence

ORD record
ord-59856de9f17448f2bbb374caf509331c
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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