Diethyl Ether → [2-(4-Benzyl-piperidin-1-yl)-ethyl]-carbamic acid tert-butyl ester

HRID 2223710Notes

Reaction equation

HRID 2223710 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]([O:18][C:19](=[O:24])[NH:20][CH2:21][CH2:22]Br)([CH3:17])([CH3:16])[CH3:15].CCN(C(C)C)C(C)C.CCOCC>C1COCC1.CCOC(C)=O.CCCCCCC>[C:14]([O:18][C:19](=[O:24])[NH:20][CH2:21][CH2:22][N:11]1[CH2:12][CH2:13][CH:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH2:10]1)([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 317384-BenzylpiperidineHCID 81531DiisopropylethylamineHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

Product 1

HCID 59715914[2-(4-Benzyl-piperidin-1-yl)-ethyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

A mixture of 4-benzyl-piperidine (876 mg, 5.0 mmol), (2-bromo-ethyl)-carbamic acid tert-butyl ester (1.12 g, 5.0 mmol) and DIPEA (650 mg, 5 mmol) in THF (30 mL) is heated at reflux for 15 h. The solution is poured into ether (150 mL) and extracted with saturated Na2CO3 (2×50 mL) and brine (30 mL), dried (Na2SO4), filtered and concentrated to provide a crude oil. Flash chromatography (EtOAc/heptane: 3/2) provides the title compound.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 15 h
  3. extractionextracted with saturated Na2CO3 (2×50 mL) and brine (30 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto provide a crude oil

Sources & evidence

ORD record
ord-81a7ef2aa908458ba4e3b397ee856c21
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

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