1-Phenethylamine, (+)- → HCID 58174049, compound

HRID 1711982Notes

Reaction equation

HRID 1711982 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][C:13]=2[O:22][S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24])=[N:4][N:3]=1.[C:30]1([C@H:36]([NH2:38])[CH3:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[C:30]1([C@H:36]([NH:38][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:15]=[CH:14][C:13]=3[O:22][S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24])=[N:4][N:3]=2)[CH3:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 6431891-Phenethylamine, (+)-HCID 58174052HCID 58174052, compound

Product 1

HCID 58174049HCID 58174049, compoundYield 93.8%

Conditions

Temperature
23 °C

Procedure

A solution of trifluoromethanesulfonic acid 1-(4-chlorophthalazin-1-yl)-naphthalen-2-yl ester (4.9 g, 11 mmol) in (R)-1-phenylethylamine (7.2 ml, 56 mmol) was stirred for 4 hrs at 120° C., then cooled to 23° C. The resulting viscous mixture was purified by flash chromatography on silica gel (toluene/EtOAc 7:1) to give 5.4 g of the title compound as a light brown solid as a 1:1 mixture of diastereomers. (yield: 93%)

Workup

  1. customThe resulting viscous mixture was purified by flash chromatography on silica gel (toluene/EtOAc 7:1)

Sources & evidence

ORD record
ord-88a585da7bb840a8bd058db0120124fc
Source dataset
uspto-grants-2010_09
Patent number
US07790882B2

Reaction notes

Loading…