Imidazole → 4-(3-Hydroxypropyloxymethyl)piperidine

HRID 1282002Notes

Reaction equation

HRID 1282002 reaction equation
Br[CH2:2][CH2:3][CH2:4][OH:5].Cl[Si](C(C)C)(C(C)C)[CH:8]([CH3:10])[CH3:9].N1[CH:21]=[CH:20][N:19]=[CH:18]1.[OH2:22]>C(Cl)Cl>[OH:22][CH2:2][CH2:3][CH2:4][O:5][CH2:9][CH:8]1[CH2:10][CH2:18][NH:19][CH2:20][CH2:21]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 123083-Bromo-1-propanolHCID 139400Triisopropylsilyl chloride

Product 1

HCID 184234304-(3-Hydroxypropyloxymethyl)piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5.0 g (36 mmol) of 3-bromopropanol, 1.04 g (54 mmol) of chlorotriisopropylsilane, and 7.1 g (104 mmol) of imidazole in 50 mL of CH2Cl2 was stirred for 3 d. To the reaction mixture was added 100 mL of H2O and the mixture was extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ethyl acetate=19:1) to give the title compound.

Workup

  1. extractionthe mixture was extracted with CH2Cl2
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chromatography (silica, hexanes:ethyl acetate=19:1)

Sources & evidence

ORD record
ord-f0ae9088b0cc4147983ea63e2b53f728
Source dataset
uspto-grants-2002_09
Patent number
US06455548B2

Reaction notes

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