Triethylamine → 1,3-dihydro-1-[2-[4-(hydroxymethyl)-1-piperidinyl]ethyl]-3-(1-methylethyl)-2H-imidazol-2-one

HRID 1635048Notes

Reaction equation

HRID 1635048 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH:8]=[CH:7][N:6]([CH:9]([CH3:11])[CH3:10])[C:5]1=[O:12].Cl.[NH:14]1[CH2:19][CH2:18][CH:17]([CH2:20][OH:21])[CH2:16][CH2:15]1.C(N(CC)CC)C>CN(C=O)C>[OH:21][CH2:20][CH:17]1[CH2:18][CH2:19][N:14]([CH2:2][CH2:3][N:4]2[CH:8]=[CH:7][N:6]([CH:9]([CH3:11])[CH3:10])[C:5]2=[O:12])[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 226627621-(2-chloroethyl)-1,3-dihydro-3-(1-methylethyl)-2H-imidazol-2-oneHCID 24191744(Piperidin-4-yl)methanol--hydrogen chloride (1/1)

Product 1

HCID 226627641,3-dihydro-1-[2-[4-(hydroxymethyl)-1-piperidinyl]ethyl]-3-(1-methylethyl)-2H-imidazol-2-oneYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-(2-chloroethyl)-1,3-dihydro-3-(1-methylethyl)-2H-imidazol-2-one (12 g), 4-piperidinemethanol hydrochloride (9.1 g), N,N-diethylethanamine (21 ml) and KI (catalytic amount) in DMF (200 ml) was stirred for 20 hours at 70° C. The reaction mixture was cooled and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 95/5). The pure fractions were collected and the solvent was evaporated, yielding 6.9 g (43%) 1,3-dihydro-1-[2-[4-(hydroxymethyl)-1-piperidinyl]ethyl]-3-(1-methylethyl)-2H-imidazol-2-one (intermediate 3).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solvent was evaporated
  3. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 95/5)
  4. customThe pure fractions were collected
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-282bf7473ef74aafa78ea5935a9c93a1
Source dataset
uspto-grants-2003_01
Patent number
US06509339B2

Reaction notes

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