Potassium Carbonate → HCID 21413252, compound

HRID 437228Notes

Reaction equation

HRID 437228 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 isopropyl alcohol (75 ml.) with 4-benzamidopiperidine (1.032 g.) and anhydrous potassium carbonate (1.037 g.). The mixture was filtered hot, refrigerated and 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. filtrationrefrigerated and 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-e546888bc48744a7a7623be085a398b8
Source dataset
uspto-grants-1977_06
Patent number
US04029801

Reaction notes

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