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

HRID 1399899Notes

Reaction equation

HRID 1399899 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

4

Reactant 2

HCID 222AmmoniaHCID 167845312-[(Oxiran-2-yl)methyl]-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 167907201-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-olYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
8 °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 8° 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

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

Sources & evidence

ORD record
ord-6ad48f983fd04b4799b8be0a9239d508
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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