Hydrochloric Acid → 2-Propyn-1-amine, N-methyl-3-[4-(trifluoromethoxy)phenyl]-

HRID 751233Notes

Reaction equation

HRID 751233 reaction equation
Cl.O1CCOCC1.C(O[C:13](=O)[N:14](C)[CH2:15][C:16]#[C:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=1)(C)(C)C>ClCCl>[CH3:13][NH:14][CH2:15][C:16]#[C:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]([F:26])([F:27])[F:28])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68824454Methyl-[3-(4-trifluoromethoxy-phenyl)-prop-2-ynyl]-carbamic acid tert-butyl ester

Product 1

HCID 688239102-Propyn-1-amine, N-methyl-3-[4-(trifluoromethoxy)phenyl]-Yield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 4 M solution of HCl in dioxane (330 μl, 1 mmol) was added at ambient temperature to a solution of methyl-[3-(4-trifluoromethoxy-phenyl)-prop-2-ynyl]-carbamic acid tert-butyl ester (50 mg, 0.15 mmol) in dichloromethane (0.5 ml). The reaction mixture was stirred for 3 h at ambient temperature. The solvent was removed under reduced pressure and the residue crystallized from dichloromethane/heptane to yield 20 mg (90 μmol, 57%) of the title compound as brown crystals.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue crystallized from dichloromethane/heptane

Sources & evidence

ORD record
ord-27d5c4ee00c6497c8dd7f5f19a83ecba
Source dataset
uspto-grants-2008_07
Patent number
US07405236B2

Reaction notes

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