Dichloromethane → 3-(1-Benzylpiperidin-4-yl)-3,4-dihydroquinazolin-2-amine

HRID 1766184Notes

Reaction equation

HRID 1766184 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][NH:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][CH2:11]1.[C:23](Br)#[N:24].ClCCl.[OH-].[Na+]>C(O)C>[NH2:24][C:23]1[N:9]([CH:10]2[CH2:11][CH2:12][N:13]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:14][CH2:15]2)[CH2:8][C:3]2[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=2)[N:1]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10476Cyanogen BromideHCID 14798Sodium HydroxideHCID 13051020N-((2-aminophenyl)methyl)-1-benzylpiperidin-4-amine

Product 1

HCID 211099063-(1-Benzylpiperidin-4-yl)-3,4-dihydroquinazolin-2-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 10.0 g (33.85 mmol) of N-[(2-aminophenyl)methyl]-1-(phenylmethyl)-4-piperidineamine in 150 ml of anhydrous ethanol was combined with 4.0 g (37.76 mmol) of bromocyanogen added batchwise. The mixture was left to stand overnight at ambient temperature, the ethanol was eliminated in vacuo and the residue was distributed between dichloromethane and 1N sodium hydroxide solution. After working up in the conventional way, 9.3 g (86% of theoretical) of colourless crystals were obtained, Rf 0.4 (El D), which were further processed without any additional purification.

Workup

  1. additionadded batchwise
  2. waitThe mixture was left
  3. customwere obtained
  4. customRf 0.4 (El D), which were further processed without any additional purification

Sources & evidence

ORD record
ord-2af62797e3954dcba058a9416d5e04e2
Source dataset
uspto-grants-2007_06
Patent number
US07230001B1

Reaction notes

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