Tetrahydrofuran → 2(1h)-Quinazolinone,3,4-dihydro-8-methoxy-3-[1-(phenylmethyl)-4-piperidinyl]-

HRID 2250256Notes

Reaction equation

HRID 2250256 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19](OC)[C:3]=1[CH2:4][NH:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1.[C:25](C1NC=CN=1)(C1NC=CN=1)=[O:26].[O:37]1CCC[CH2:38]1>>[CH2:12]([N:9]1[CH2:10][CH2:11][CH:6]([N:5]2[CH2:4][C:3]3[C:2](=[C:22]([O:37][CH3:38])[CH:21]=[CH:20][CH:19]=3)[NH:1][C:25]2=[O:26])[CH2:7][CH2:8]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 21102118(2-Amino-6-methoxy-benzyl)-(1-benzyl-piperidin-4-yl)-amine

Product 1

HCID 211021562(1h)-Quinazolinone,3,4-dihydro-8-methoxy-3-[1-(phenylmethyl)-4-piperidinyl]-Yield 68%

Conditions

Temperature
0 °C

Procedure

A stirred solution of (2-amino-6-methoxy-benzyl)-(1-benzyl-piperidin-4-yl)-amine (0.2 g, 0.62 mmol) in tetrahydrofuran (3 mL) at 0° C. was treated with carbonyl diimidazole (99 mg, 0.62 mmol). The reaction was stirred for 30 min at 0° C. and at reflux for 1 h. After cooling to room temperature, the solvent was evaporated and the residue purified by column to afford 150 mg (68%) of the desired product. LC/MS: tR=1.41 min, 352.30 (MH)+.

Workup

  1. temperatureat reflux for 1 h
  2. temperatureAfter cooling to room temperature
  3. customthe solvent was evaporated
  4. customthe residue purified by column

Sources & evidence

ORD record
ord-27048f352e314ff8937a94abba216b22
Source dataset
uspto-grants-2008_01
Patent number
US07314883B2

Reaction notes

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