Hydrochloric Acid → 2-[(Propylamino)methyl]phenol

HRID 38016Notes

Reaction equation

HRID 38016 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][N:5]([CH2:13][CH2:14][CH3:15])C(=O)OC(C)(C)C.Cl>CO>[CH2:13]([NH:5][CH2:4][C:3]1[CH:16]=[CH:17][CH:18]=[CH:19][C:2]=1[OH:1])[CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66959640Tert-butyl 2-hydroxybenzyl(propyl)carbamate

Product 1

HCID 129952192-[(Propylamino)methyl]phenolYield 108.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of tert-butyl 2-hydroxybenzyl(propyl)carbamate (89 g, 0.34 mol) in MeOH (400 mL) was bubbled with HCl gas. After stirring for 5 h at room temperature, the reaction mixture was concentrated under reduced pressure to afford 61 g (90%) of 2-((propylamino)methyl)phenol as HCl salt.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1773d168b0c04d3cb8c937689a385a1d
Source dataset
uspto-grants-2013_09
Patent number
US08524702B2

Reaction notes

Loading…