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

HRID 2217268Notes

Reaction equation

HRID 2217268 reaction equation
[CH3:1][N:2]([CH3:30])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[N:10]([CH:17]1[CH2:22][CH2:21][N:20](CC3C=CC=CC=3)[CH2:19][CH2:18]1)[CH2:9]2.[H][H]>[OH-].[Pd+2].[OH-].CO>[CH3:1][N:2]([CH3:30])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[N:10]([CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)[CH2:9]2

Participants

5

Reactant 2

HCID 179587003,4-dihydro-6-[2-(dimethylamino)ethoxy]-3-(1-phenylmethyl-4-piperidinyl)-2(1H)-quinazolinoneHCID 178418361HCID 178418361, compound

Product 1

HCID 179586863,4-dihydro-6-[2-(dimethylamino)ethoxy]-3-(4-piperidinyl)-2(1H)-quinazolinone

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.9 g (0.0022 mol) of 3,4-dihydro-6-[2-(dimethylamino)ethoxy]-3-(1-phenylmethyl-4-piperidinyl)-2(1H)-quinazolinone, 10 mL methanol, and 0.5 g palladium(II) hydroxide (Pearlman's catalyst) was hydrogenated until the uptake of hydrogen ended. The catalyst was filtered off, the filtrate was evaporated down in vacuo, and the residue remaining was used in the next step without any further purification. Yield: 0.6 g (86% of theoretical). IR (KBr): 1662 (C═O) cm−1; MS: M+=318.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated down in vacuo
  3. customthe residue remaining was used in the next step without any further purification

Sources & evidence

ORD record
ord-072a7b45ccac44d5bd79958f6e0242ff
Source dataset
uspto-grants-2008_08
Patent number
US07407963B2

Reaction notes

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