Ammonia → 1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol

HRID 1051525Notes

Reaction equation

[O:1]1[CH2:3][CH:2]1[CH2:4][N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1.[NH3:15]>CCO>[NH2:15][CH2:3][CH:2]([OH:1])[CH2:4][N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2-(oxiran-2-ylmethyl)-1,2,3,4-tetrahydroisoquinoline (17 g, 0.09 mol) in EtOH (300 mL) had NH3 gas bubbled to the solution at −78° C. The reaction mixture was then sealed and heated to 80° C. for 3 h. After completion of the reaction, the mixture was concentrated and the resulting crude product used in next step without further purification (18 g, Yield 96%). LCMS (m/z): 207.1 [M+H]+.

Workup

custombubbled to the solution at −78° C
customThe reaction mixture was then sealed
customAfter completion of the reaction
concentrationthe mixture was concentrated
customthe resulting crude product used in next step without further purification (18 g, Yield 96%)

Sources & evidence

ORD record: ord-3e329cc15f9e41e48e5edad35ee5cb18
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388173B2

Reaction notes

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