1-Benzyl-4-piperidone → 1-(Phenylmethyl)spiro[piperidine-4,2'(1'H)-quinazoline]-4'-amine dihydrochloride

HRID 1418393Notes

Reaction equation

HRID 1418393 reaction equation
[ClH:1].Cl.[NH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([NH2:8])=[NH:7].[CH2:13]([N:20]1[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C.Cl>[ClH:1].[ClH:1].[C:14]1([CH2:13][N:20]2[CH2:25][CH2:24][C:23]3([N:7]=[C:6]([NH2:8])[C:5]4[C:4](=[CH:12][CH:11]=[CH:10][CH:9]=4)[NH:3]3)[CH2:22][CH2:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 192201-Benzyl-4-piperidoneHCID 669893132-Aminobenzamidine dihydrochloride

Product 1

HCID 675696971-(Phenylmethyl)spiro[piperidine-4,2'(1'H)-quinazoline]-4'-amine dihydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 2-aminobenzamidine dihydrochloride (2.0 g, 9.6 mmol) and N-benzyl4-piperidone (2.1 ml, 11.5 mmol) in ethanol (40 ml) and HCl (1M in Et2O, 5 ml) was heated at 70° C. for 20 h. Evaporation and flash column chromatography on untreated alumina eluting with DCM/methanol (10:1) gave after trituration from ether a yellow solid, MS (+EI) 307 ([M+H]+), 1H NMR (d6 -DMSO) 9.99 (1H, s), 9.1 (1H, s), 8.5 (1H, s), 7.81 (1H, d), 7.53 (1H, s), 7.46 (1H, t), 7.2-7.4 (5H, m), 6.89 (1H, d), 6.79 (1H, dd), 3.52 (2H, s), 2.4-2.6 (4H, m), 1.91 (2H, m), 1.82 (2H, m).

Workup

  1. customEvaporation and flash column chromatography on untreated alumina eluting with DCM/methanol (10:1)
  2. customgave after trituration from ether a yellow solid, MS (+EI) 307 ([M+H]+), 1H NMR (d6 -DMSO) 9.99 (1H, s), 9.1 (1H, s), 8.5 (1H, s), 7.81 (1H, d), 7.53 (1H, s), 7.46 (1H, t), 7.2-7.4 (5H, m), 6.89 (1H, d), 6.79 (1H, dd), 3.52 (2H, s), 2.4-2.6 (4H, m), 1.91 (2H, m), 1.82 (2H, m)

Sources & evidence

ORD record
ord-d24765d20b6345df889c99a5a5d7fa0a
Source dataset
uspto-grants-1999_03
Patent number
US05883102

Reaction notes

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