Triethylamine → Ethyl 1-[2-(4-hydroxyphenoxy)ethyl]piperidine-4-carboxylate

HRID 1807458Notes

Reaction equation

HRID 1807458 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[NH:12]1[CH2:22][CH2:21][CH:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][CH2:13]1.CCN(CC)CC>CC#N>[OH:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][N:12]2[CH2:22][CH2:21][CH:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][CH2:13]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70770Ethyl 4-piperidinecarboxylateHCID 128339324-(2-Bromoethoxy)phenol

Product 1

HCID 57448391Ethyl 1-[2-(4-hydroxyphenoxy)ethyl]piperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of 4-(2-bromo-ethoxy)-phenol (600 mg, 2.77 mmol) and ethyl isonipecotate (470 μL, 3.06 mmol) in CH3CN (12 mL) was added Et3N (768 μL, 5.54 mmol). The resultant mixture was stirred at rt overnight and then concentrated to afford the title compound, which was used immediately in the next step. MS (ESI): mass calcd. for C16H23NO4, 293.16; m/z found, 294.1 [M+H]+.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-8b505abd7bba402480968707b384131a
Source dataset
uspto-grants-2013_01
Patent number
US08357684B2

Reaction notes

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