Piperidine → 1-{3-[4-(4,4-Dimethyl-4,5-dihydro-1,3-oxazol-2-yl)phenoxy]propyl}piperidine

HRID 251440Notes

Reaction equation

HRID 251440 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][CH2:14][C:15]([CH3:18])([CH3:17])[N:16]=2)=[CH:8][CH:7]=1.[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>>[CH3:17][C:15]1([CH3:18])[CH2:14][O:13][C:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:7][CH:8]=2)=[N:16]1

Participants

3

Reactant 2

HCID 8082PiperidineHCID 11950718HCID 11950718, compound

Product 1

HCID 117024471-{3-[4-(4,4-Dimethyl-4,5-dihydro-1,3-oxazol-2-yl)phenoxy]propyl}piperidineYield 83%

Conditions

Temperature
100 °C

Procedure

A mixture of 2-[4-(3-chloropropoxy)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole ax10 (0.5 g, 1.87 mmol, 1 eq) and piperidine (0.37 ml, 3.73 mmol, 2 eq) is stirred in a sealed tube at 100° C. overnight. The mixture is then concentrated under vacuum to give 0.8 g of an orange solid. This solid is purified by chromatography on silica gel (eluent: dichloromethane/ethanol 95:5) to obtain 0.49 g of 1-{3-[4-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)phenoxy]propyl}piperidine 1 as an orange oil.

Workup

  1. concentrationThe mixture is then concentrated under vacuum

Sources & evidence

ORD record
ord-fa072112f043442cababba1da0c1bc8b
Source dataset
uspto-grants-2011_01
Patent number
US07863450B2

Reaction notes

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