1-Butanol → (R)-1-(1-Phenylethylamino)-4-(4-pyridylmethyl)phthalazine dihydrochloride

HRID 49864

Reaction equation

HRID 49864 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:4][N:3]=1.[C:19]1([C@@H:25]([NH2:27])[CH3:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(O)CCC>O>[ClH:1].[ClH:1].[C:19]1([C@H:25]([NH:27][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[N:4][N:3]=2)[CH3:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 2631-ButanolHCID 758181-Phenethylamine, (-)-HCID 19446091-Chloro-4-(4-pyridinylmethyl)phthalazine

Product 1

HCID 69837621(R)-1-(1-Phenylethylamino)-4-(4-pyridylmethyl)phthalazine dihydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 0.511 g (2 mmol) 1-chloro-4-(4-pyridylmethyl)phthalazine, 1.273 ml (10 mmol) (S)-1 phenylethylamine and 5 ml 1-butanol is stirred for 40 h at 110° C. After processing as described in Example 12 and equilibration for 65 hours at 20° C. and in room atmosphere, title compound is obtained with a water content of 10.53%; m.p. 190° C. (decomp.); ESI-MS: (M+H)+=341; [α]D20=+38.4±0.70 (c=1.507%, methanol).

Workup

  1. waitas described in Example 12 and equilibration for 65 hours at 20° C. and in room atmosphere

Sources & evidence

ORD record
ord-0e3f3997fada4ff0972d23f85223536c
Source dataset
uspto-grants-2004_03
Patent number
US06710047B2

Linked notes

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