2-(Dimethylamino)ethanol → 3,4-dihydro-6-[2-(dimethylamino)ethoxy]-3-(1-phenylmethyl-4-piperidinyl)-2(1H)-quinazolinone

HRID 2217271Notes

Reaction equation

HRID 2217271 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[N:6]([CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:14]1)[CH2:5]2.[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[N:6]([CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:14]1)[CH2:5]2

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 179586923,4-dihydro-6-hydroxy-3-(1-phenylmethyl-4-piperidinyl)-2(1H)-quinazolinone

Product 1

HCID 179587003,4-dihydro-6-[2-(dimethylamino)ethoxy]-3-(1-phenylmethyl-4-piperidinyl)-2(1H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.1 g (3.26 mmol) of 3,4-dihydro-6-hydroxy-3-(1-phenylmethyl-4-piperidinyl)-2(1H)-quinazolinone, 50 mL of tetrahydrofuran, 0.30 g (3.366 mmol) of 2-dimethylaminoethanol, 0.94 g (3.584 mmol) of triphenylphosphine, and 0.56 g (3.216 mmol) of azodicarboxylic acid ester was stirred for one hour at ambient temperature, 6 hours at reflux temperature and another 13 hours at ambient temperature. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel (30-60 μm) using dichloromethane/EE/cyclohexane/methanol/concentrated ammonia 60/16/5/5/0.6 v/v/v/v/v as eluant. Working up the corresponding fractions yielded 0.9 g (69% of theoretical) of a colorless crystalline substance, Rf=0.47 (dichloromethane/EE/cyclohexane/methanol/concentrated ammonia 60/16/5/5/0.6 v/v/v/v/v).

Workup

  1. temperatureat reflux temperature
  2. customanother 13 hours
  3. customat ambient temperature
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by column chromatography on silica gel (30-60 μm)
  6. customWorking up the corresponding fractions yielded 0.9 g (69% of theoretical) of a colorless crystalline substance, Rf=0.47 (dichloromethane/EE/cyclohexane/methanol/concentrated ammonia 60/16/5/5/0.6 v/v/v/v/v)

Sources & evidence

ORD record
ord-57b329540eb74834b2c44620084e42eb
Source dataset
uspto-grants-2008_08
Patent number
US07407963B2

Reaction notes

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