Hydrochloric Acid → HCID 70025339, compound

HRID 1489577Notes

Reaction equation

HRID 1489577 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 N 2 at 100° C. for 90 min. On cooling the reaction mixture is diluted with CHCl3 (10 mL), and is shaken with dilute hydrochloric acid (0.2M, 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-phenylethylamino)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-f8cc0bf1261a4bf68490ba8bb55c57df
Source dataset
uspto-grants-1997_10
Patent number
US05679683

Reaction notes

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