Triethylamine → 1-Cyclopropanecarbonyl-4-hydroxypiperidine

HRID 1363618Notes

Reaction equation

HRID 1363618 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.C(OCC1N(C[C:25]2([OH:31])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)C2C3C=CC=CC=3N=CC=2N=1)C.C(N(CC)CC)C>ClCCl>[CH:1]1([C:4]([N:28]2[CH2:29][CH2:30][CH:25]([OH:31])[CH2:26][CH2:27]2)=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 575154124-[(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidin-4-ol

Product 1

HCID 149949671-Cyclopropanecarbonyl-4-hydroxypiperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere cyclopropanecarbonyl chloride (0.84 mL, 9.25 mmol) was added dropwise to a chilled mixture of 4-[(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidin-4-ol (3.00 g, 8.81 mmol), triethylamine (1.47 mL, 10.6 mmol) and dichloromethane (90 mL). The reaction mixture was allowed to warm to ambient temperature. After 2 hours the reaction mixture was washed with water. The organic layer was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel eluting with 90/10 dichloromethane/methanol) to provide 3.16 g of 4-[2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]-1-(cyclopropylcarbonyl)piperidin-4-ol as a light orange frothy solid.

Workup

  1. washAfter 2 hours the reaction mixture was washed with water
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography (silica gel eluting with 90/10 dichloromethane/methanol)

Sources & evidence

ORD record
ord-679e2ef769754ba597c2064794f71b4a
Source dataset
uspto-grants-2011_02
Patent number
US07884207B2

Reaction notes

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