Acetyl chloride → 1-acetyl-4-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}piperidin-4-ol

HRID 1363566Notes

Reaction equation

HRID 1363566 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH2:5]([O:7][CH2:8][C:9]1[N:10]([CH2:22][C:23]2([OH:29])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[C:11]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:21]=1)[CH3:6].C(N(CC)CC)C>ClCCl>[C:1]([N:26]1[CH2:27][CH2:28][C:23]([CH2:22][N:10]2[C:11]3[C:20]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[N:14]=[CH:13][C:12]=3[N:21]=[C:9]2[CH2:8][O:7][CH2:5][CH3:6])([OH:29])[CH2:24][CH2:25]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 575154124-[(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidin-4-ol

Product 1

HCID 575154131-acetyl-4-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}piperidin-4-olYield 64.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Acetyl chloride (0.57 mL, 8.1 mmol) was added to a suspension of 4-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}piperidin-4-ol (2.50 g, 7.34 mmol) and triethylamine (1.50 mL, 11.0 mmol) in dichloromethane (37 mL) at rt. The resulting solution was stirred for 1 h. The solution was diluted with dichloromethane (100 mL) and washed with water (50 mL) and saturated aqueous sodium bicarbonate (50 mL). The combined aqueous layers were back-extracted with dichloromethane (50 mL). The combined organic layers were washed with brine (50 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to a brown foam. Purification by flash chromatography (silica gel, eluted with 10% methanol/dichloromethane) provided 1-acetyl-4-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}piperidin-4-ol as a white foam (1.8 g, 64%).

Workup

  1. washwashed with water (50 mL) and saturated aqueous sodium bicarbonate (50 mL)
  2. extractionThe combined aqueous layers were back-extracted with dichloromethane (50 mL)
  3. washThe combined organic layers were washed with brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to a brown foam
  7. customPurification
  8. washby flash chromatography (silica gel, eluted with 10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-37a1230db2324384819870d45cf5df31
Source dataset
uspto-grants-2011_02
Patent number
US07884207B2

Reaction notes

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