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

HRID 547352Notes

Reaction equation

HRID 547352 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-6b5970e75c0b4eb69c83f7c71f321063
Source dataset
uspto-grants-2011_05
Patent number
US07939527B2

Reaction notes

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