Hydrochloric Acid → 4-(1-Benzyl-piperidin-4-ylidenemethyl)-benzimidic acid ethyl ester

HRID 1663237Notes

Reaction equation

HRID 1663237 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(Cl)Cl.Cl.[CH2:28]([OH:30])[CH3:29]>>[CH2:28]([O:30][C:19](=[NH:20])[C:18]1[CH:17]=[CH:16][C:15]([CH:14]=[C:11]2[CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9][CH2:10]2)=[CH:22][CH:21]=1)[CH3:29]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6212ChloroformHCID 674356554-(1-Benzyl-piperidin-4-ylidenemethyl)-benzonitrile

Product 1

HCID 674362034-(1-Benzyl-piperidin-4-ylidenemethyl)-benzimidic acid ethyl esterYield 92.4%

Procedure

A mixture of 4-(1-benzyl-piperidin-4-ylidenemethyl)-benzonitrile (14 g, 48.6 mmol), chloroform (10 mL) and 6 M hydrogen chloride in ethanol (300 mL) was stirred at room temperature for 48 hours. The solution was concentrated in vacuo, the remaining solid was repeatedly dissolved in ethanol (400 mL) and concentrated in vacuo to yield 16.4 g (92.4%) of the title compound, which was used in the next steps without further purification.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe remaining solid was repeatedly dissolved in ethanol (400 mL)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-491d251fbdd64308bae3659291581e66
Source dataset
uspto-grants-2011_10
Patent number
US08034827B2

Reaction notes

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