(2E)-3-(4-Cyanophenyl)-2-propenoic acid → 4-[(E)-3-Oxo-3-((S)-2-((piperidin-1-yl)methyl)pyrrolidin-1-yl)propenyl]benzonitrile

HRID 2212036Notes

Reaction equation

HRID 2212036 reaction equation
[C:1]([C:3]1[CH:13]=[CH:12][C:6](/[CH:7]=[CH:8]/[C:9]([OH:11])=O)=[CH:5][CH:4]=1)#[N:2].[NH:14]1[CH2:18][CH2:17][CH2:16][C@H:15]1[CH2:19][N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>>[O:11]=[C:9]([N:14]1[CH2:18][CH2:17][CH2:16][C@H:15]1[CH2:19][N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)/[CH:8]=[CH:7]/[C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 735786(2E)-3-(4-Cyanophenyl)-2-propenoic acidHCID 7022796(S)-1-(pyrrolidin-2-ylmethyl)piperidine

Product 1

HCID 586971914-[(E)-3-Oxo-3-((S)-2-((piperidin-1-yl)methyl)pyrrolidin-1-yl)propenyl]benzonitrile

Procedure

150 mg of the title compound were synthesized as described for (E)-3-(4-bromophenyl)-1-((S)-2-((pyrrolidin-1-yl)methyl)pyrrolidin-1-yl)propenone, using (E)-4-cyanocinnamic acid instead of (E)-4-bromocinnamic acid and 1-(((S)-pyrrolidin-2-yl)methyl)piperidine instead of (S)-2-((pyrrolidin-1-yl)methyl)pyrrolidine.

Sources & evidence

ORD record
ord-37a99e3711974eaf88aa098d9bce058a
Source dataset
uspto-grants-2006_09
Patent number
US07101898B2

Reaction notes

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