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

HRID 1777085Notes

Reaction equation

HRID 1777085 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
80 °C

Procedure

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

Workup

  1. customat −78° C.
  2. customThe reaction mixture was then sealed
  3. concentrationThe reaction mixture was concentrated
  4. customthe crude product was used in next step without further purification (18 g, Yield 96%)

Sources & evidence

ORD record
ord-c81d0a2bb1654653954c4149c0a065cc
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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