2-Bromoethanol → HCID 10681218, compound

HRID 482294Notes

Reaction equation

HRID 482294 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.Br[CH2:16][CH2:17][OH:18].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:9]1([CH2:8][N:5]2[CH2:6][CH2:7][CH:2]([NH:1][CH2:16][CH2:17][OH:18])[CH2:3][CH2:4]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 81531DiisopropylethylamineHCID 4158521-Benzyl-4-piperidylamine

Product 1

HCID 10681218HCID 10681218, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-amino-1-benzylpiperidine (2.13 g, 11.2 mmol) and 2-bromoethanol (0.15 g, 4.08 mmol) in anhydrous CH2Cl2 (20 ml) was added Hunig's base (2.6 ml, 5.7 mmol). The solution was refluxed for 24 hours. After evaporating off CH2Cl2, the crude material was purified by silica flash chromatography to afford 2-[[1-(phenylmethyl)-4-piperidinyl]amino]ethanol (0.88 g, 3.8 mmol) with 92% yield. FAB Mass [M+1]+35Cl 235.

Workup

  1. temperatureThe solution was refluxed for 24 hours
  2. customAfter evaporating off CH2Cl2
  3. customthe crude material was purified by silica flash chromatography

Sources & evidence

ORD record
ord-ea1492ebbb294758af4bd4faa169a82f
Source dataset
uspto-grants-1998_08
Patent number
US05795894

Reaction notes

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