Triethylamine → 6-{3-[4-(4-fluorobenzyl)piperid-1-yl]propyl}-3H-benzoxazol-2-one

HRID 1266188Notes

Reaction equation

HRID 1266188 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]1[CH:14]=[CH:13][C:8]2[NH:9][C:10](=[O:12])[O:11][C:7]=2[CH:6]=1.Cl.[F:16][C:17]1[CH:29]=[CH:28][C:20]([CH2:21][CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:19][CH:18]=1.C(N(CC)CC)C>C(O)C>[F:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:21][CH:22]2[CH2:23][CH2:24][N:25]([CH2:2][CH2:3][CH2:4][C:5]3[CH:14]=[CH:13][C:8]4[NH:9][C:10](=[O:12])[O:11][C:7]=4[CH:6]=3)[CH2:26][CH2:27]2)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 110637386-(3-chloropropyl)-2(3H)-BenzoxazoloneHCID 170394924-[(4-Fluorophenyl)methyl]piperidine hydrochloride

Product 1

HCID 97994146-{3-[4-(4-fluorobenzyl)piperid-1-yl]propyl}-3H-benzoxazol-2-oneYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 5.5 g of 6-(3-chloropropyl)-3H-benzoxazol-2-one in 50 ml of ethanol is admixed with 5.7 g of 4-(4-fluorobenzyl)piperidine hydrochloride and 7.2 ml of triethylamine. The mixture is stirred under reflux for one hour and subjected to customary workup to give 8.5 g of 6-{3-[4-(4-fluorobenzyl)piperid-1-yl]propyl}-3H-benzoxazol-2-one, m.p. 105-107°.

Workup

  1. temperatureunder reflux for one hour

Sources & evidence

ORD record
ord-7e66bd83618c47ec84d4ca2ddb4de1d4
Source dataset
uspto-grants-2003_04
Patent number
US06548516B1

Reaction notes

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