1-Phenethylamine, (+)- → HCID 86602158, compound

HRID 1711984Notes

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]=[C:19]([O:22][CH3:23])[CH:20]=3)[CH:15]=[CH:14][C:13]=2[O:24][S:25]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26])=[N:4][N:3]=1.[C:32]1([C@H:38]([NH2:40])[CH3:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[CH3:23][O:22][C:19]1[CH:20]=[C:21]2[C:16]([CH:15]=[CH:14][C:13]([O:24][S:25]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26])=[C:12]2[C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([NH:40][C@@H:38]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH3:39])=[N:3][N:4]=2)=[CH:17][CH:18]=1

Participants

Reactant 2

HCID 6431891-Phenethylamine, (+)-

HCID 86602157HCID 86602157, compound

Product 1

HCID 86602158HCID 86602158, compoundYield 80.9%

Conditions

Temperature: 23 °C

Procedure

A solution of trifluoromethanesulfonic acid 1-(4-chlorophthalazin-1-yl)-7-methoxynaphthalen-2-yl ester (2.2 g, 4.7 mmol) in (R)-1-phenylethylamine (3.5 ml, 27 mmol) was stirred for 8 hrs at 130° C., then cooled to 23° C. The resulting viscous mixture was purified by flash chromatography on silica gel (toluene/EtOAc 5:1 to 3:1) to give 2.1 g (3.8 mmol) of the title compound as a 1:1 mixture of diastereomers as a light brown foam.

Workup

customThe resulting viscous mixture was purified by flash chromatography on silica gel (toluene/EtOAc 5:1 to 3:1)

Sources & evidence

ORD record: ord-5ca8522d87534b33a726110be54ae0ed
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790882B2

Reaction notes

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