Potassium Carbonate → HCID 21413252, compound

HRID 1730339Notes

Reaction equation

HRID 1730339 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:13]([NH:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:25]2[CH2:26][CH2:27][CH:22]([NH:21][C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:23][CH2:24]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 792664-Nitrophenethyl bromideHCID 118120N-4-Piperidylbenzamide

Product 1

HCID 21413252HCID 21413252, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

p-Nitrophenylethyl bromide (1.15 g.) was refluxed for 20 hours in isopropylalcohol (75 ml.) with 4-benzamidopiperidine (1.032 g.) and anhydrous potassium carbonate (1.037 g.). The mixture was filtered hot, refrigeratedand product was filtered off (547 mg.), washed with cold isopropyl alcohol and ether. The filtrate was evaporated to yield more product (1.4 g.). Recrystallisation from a mixture of benzene and petroleum ether (b.p. 40°-60° C) gave the title compound, m.p. 209°-216° C. (Found: C, 68.2; H, 6.7; N, 11.8. C20H23N3O3 requires C, 68.0; H, 6.6; N, 11.9%).

Workup

  1. filtrationThe mixture was filtered hot
  2. filtrationrefrigeratedand product was filtered off (547 mg.)
  3. washwashed with cold isopropyl alcohol and ether
  4. customThe filtrate was evaporated
  5. customto yield more product (1.4 g.)
  6. customRecrystallisation
  7. additionfrom a mixture of benzene and petroleum ether (b.p. 40°-60° C)

Sources & evidence

ORD record
ord-85cd085014f54e9a8fe49ea9e535d271
Source dataset
uspto-grants-1976_11
Patent number
US03992389

Reaction notes

Loading…