1-Phenylpiperazine → HCID 178517112, compound

HRID 466992Notes

Reaction equation

HRID 466992 reaction equation
Br[CH2:2][CH:3]1[CH2:16][N:6]2[C:7](=[O:15])[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:5]2=[N:4]1.[C:17]1([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(#N)C>[C:17]1([N:23]2[CH2:28][CH2:27][N:26]([CH2:2][CH:3]3[CH2:16][N:6]4[C:7](=[O:15])[NH:8][C:9]5[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=5[C:5]4=[N:4]3)[CH2:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 70961-PhenylpiperazineHCID 178517109HCID 178517109, compound

Product 1

HCID 178517112HCID 178517112, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-bromomethyl-2,3-dihydroimidazo[1,2-c]-quinazolin-5(6H)-one (0.5 g, 1.78 mmol), N-phenylpiperazine (0.28 mL, 3.56 mmol) in acetonitrile (25 mL) was refluxed for 13 hours. The hot mixture was filtered and washed with acetonitrile (10 mL) to give 2-(4-phenyl-1-piperazinyl)methyl-2,3-dihydroimidazo[1,2-c]-quinazolin-5(6H)-one (490 mg, 76%). An analytical sample was prepared from a mixture of acetonitrile and methanol (1:1), mp 257°-258° C. ms: m/z 361 (M+). 1H NMR (300 MHz, DMSO-d6): δ2.43-2.73 (m, 7H, CH2), 3.11 (t, 3H, CH2), 3.65 (q, 1H, CH), 3.91 (t, 1H, CH), 4.41 (m, 1H, CH), 6.75 (t, 1H, Ar--H), 6.91 (d, 2H, Ar--H), 7.06 (q, 2 H, Ar--H), 7.17 (q, 2H, Ar--H), 7.48 (p, 1H, Ar--H), 7.78 (d, 1H, Ar--H), 10.53 (s, 1H, NH). Anal. Calcd for C21H23N5O: C, 69.78; H, 6.41; N, 19.38. Found: C, 69.79; H, 6.45; N, 19.37.

Workup

  1. temperaturewas refluxed for 13 hours
  2. filtrationThe hot mixture was filtered
  3. washwashed with acetonitrile (10 mL)

Sources & evidence

ORD record
ord-3229674bf7a4473091bcc0d71cf233be
Source dataset
uspto-grants-1992_10
Patent number
US05158953

Reaction notes

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