4-Piperidinecarboxamide → HCID 131722011, compound

HRID 1955202Notes

Reaction equation

HRID 1955202 reaction equation
[NH:1]1[CH2:9][CH2:8][CH:4]([C:5](N)=[O:6])[CH2:3][CH2:2]1.[F:10][C:11]1[CH:20]=[CH:19][C:14]([O:15][CH2:16][CH2:17]Br)=[CH:13][CH:12]=1.[C:21]([O-:24])([O-:23])=O.[K+].[K+]>>[C:5]([OH:15])(=[O:6])/[CH:4]=[CH:8]\[C:21]([OH:24])=[O:23].[C:14]([OH:6])(=[O:15])/[CH:19]=[CH:20]\[C:21]([OH:24])=[O:23].[F:10][C:11]1[CH:20]=[CH:19][C:14]([O:15][CH2:16][CH2:17][N:1]2[CH2:9][CH2:8][CH:4]([CH2:5][C:2]3[CH:3]=[CH:4][CH:8]=[CH:9][N:1]=3)[CH2:3][CH2:2]2)=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 37724-PiperidinecarboxamideHCID 11430Potassium CarbonateHCID 20641711-(2-Bromoethoxy)-4-fluorobenzene

Product 1

HCID 131722011HCID 131722011, compound

Procedure

The title compound was prepared from isonipecotamide, 2-(4-fluorophenoxy)ethyl bromide, and K2CO3 in four steps as a pale yellow solid, mp 114-115° C.; 1H NMR (CDCl3) 1.56-1.75 (m, 2H), 1.94 (d, J=15 Hz, 2H), 2.08-2.25 (m, 1H), 2.96-3.18 (m, 4H), 3.33-3.56 (m, 2H), 3.62-3.73 (m, 2H), 4.32 (d, J=4.8 Hz, 2H), 6.26 (s, 4H), 6.91-7.12 (m, 4H), 7.84-7.94 (m, 2H), 8.48 (td, J=7.8 and 1.5 Hz, 1H), 8.63 (d, J=6.0 Hz, 1H); Anal. Calcd for C27H31FN2O9 : C, 59.33; H, 5.71; N, 5.12. Found: C, 59.36; H, 5.68; N, 4.94.

Sources & evidence

ORD record
ord-dad2977940a8463387b5ab39b614f7f3
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

Loading…