Hydrochloric Acid → HCID 70025339, compound

HRID 1358260Notes

Reaction equation

HRID 1358260 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]=2)[N:5]=[CH:4][N:3]=1.[C:16]1([C@H:22]([NH2:24])[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CCN(CC)CC.Cl.C[O:34]C(O)C>C(Cl)(Cl)Cl>[OH2:34].[ClH:1].[C:16]1([C@H:22]([NH:24][C:2]2[C:11]3[C:6](=[CH:7][C:8]4[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=4[CH:10]=3)[N:5]=[CH:4][N:3]=2)[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 6431891-Phenethylamine, (+)-HCID 30156371-MethoxyethanolHCID 110638054-chlorobenzo[g]quinazoline

Product 1

HCID 70025339HCID 70025339, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-Chlorobenzo[g]quinazoline (107 mg, 0.5 mmol), [R]-1-phenylethylamine (72 mg, 0.6 mmol) and NEt3 (202 mg, 2.0 mmol) in stirred methoxyethanol (2 mL) are heated under N2 at 100° C. for 90 min. On cooling the reaction mixture is diluted with CHCl3 (10 ML), and is shaken with dilute hydrochloric acid (0.2 M, 15 mL). The heavy yellow precipitate is collected by Buchner filtration, rinsed with water (5 mL), and dried in vacuo at 60° C. to give 4-([R]-1-phenylethyl-amino)benzo[g]quinazoline hydrochloride hydrate (122 mg, 64%) as a yellow solid. 1H NMR (DMSO) δ14.75 (1H brs), 10.85 (1H, d, J=8.0 Hz), 9.61 (1H, s), 8.90 (1H, s), 8.36 (1H, s), 8.18 (1H, d, J=8.2 Hz), 7.82 (1H, t, J=7.6 Hz), 7.74 (1H, t, J=7.4 Hz), 7.56 (2H, d, J=7.5 KHz), 7.39 (2H, t, J=7.6 Hz), 7.30 (1H, t, J=7.4 Hz), 5.92 (1H, pentet, J=7.2 Hz), 1.76 (3H, d, J=7.2 Hz).

Workup

  1. temperatureOn cooling the reaction mixture
  2. filtrationThe heavy yellow precipitate is collected by Buchner filtration
  3. washrinsed with water (5 mL)
  4. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-5b61ca580b154ebfb5aaccd2d00b07fc
Source dataset
uspto-grants-2003_07
Patent number
US06596726B1

Reaction notes

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