Phenethylamine → 1-cyclopropyl-1,2,3,4-tetrahydroisoquinoline

HRID 1932308Notes

Reaction equation

[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:10]1([C:13](Cl)=O)[CH2:12][CH2:11]1>>[CH:10]1([CH:13]2[C:8]3[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:2][CH2:1][NH:9]2)[CH2:12][CH2:11]1

Participants

Reactant 2

HCID 1001Phenethylamine

HCID 77637Cyclopropanecarbonyl chloride

Product 1

HCID 115573681-cyclopropyl-1,2,3,4-tetrahydroisoquinoline

Procedure

In accordance with the same procedures as in Steps 1, 2, and 3 of Preparation 21, except for using phenethylamine and cyclopropanecarbonyl chloride, 1-cyclopropyl-1,2,3,4-tetrahydroisoquinoline was obtained. In accordance with the same procedures as in Preparation 20, the titled compound was obtained as pale yellow oil. (Yield: 82%) The product was used in the subsequent step without further purification.

Workup

customIn accordance with the same procedures as in Steps 1, 2, and 3 of Preparation 21

Sources & evidence

ORD record: ord-a7eaea93683c4789bbaa7d00bda74d31
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188114B2

Reaction notes

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