Ammonia → 3,4-dihydro-3-[1-(4-piperidinyl)-4-piperidinyl]-2(1H)-quinazolinone

HRID 1782704Notes

Reaction equation

HRID 1782704 reaction equation
C1(C[N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[CH2:19][CH2:18][CH:17]([N:20]4[CH2:29][C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[NH:22][C:21]4=[O:30])[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)C=CC=CC=1.N>[OH-].[OH-].[Pd+2].ClCCl.CO.C1CCCCC1>[NH:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:19][CH2:18][CH:17]([N:20]3[CH2:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[NH:22][C:21]3=[O:30])[CH2:16][CH2:15]2)[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 183211743,4-dihydro-3-[1-[1-(phenylmethyl)-4-piperidinyl]-4-piperidinyl]-2(1H)-quinazolinone

Product 1

HCID 183214343,4-dihydro-3-[1-(4-piperidinyl)-4-piperidinyl]-2(1H)-quinazolinoneYield 92%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 69163855HCID 69163855, compoundSolvent

Procedure

Prepared analogously to Example A3f) from 3,4-dihydro-3-[1-[1-(phenylmethyl)-4-piperidinyl]-4-piperidinyl]-2(1H)-quinazolinone by hydrogenolysis, but using Pearlman's catalyst, in a yield of 92% of theory. Colourless crystals, Rf=0.48 (Macherey-Nagel, POLYGRAM® SIL G/UV254ready-made films for TLC; eluant: dichloromethane/methanol/cyclohexane/conc. ammonia 68/20/10/5 v/v/v/v).

Sources & evidence

ORD record
ord-87a01a56e7674e36a17dab6713efaf0a
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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