Tert-butyl 3-(3-chlorophenyl)-3-(3-methoxypropoxy)propyl(isopropyl)carbamate → 3-(3-chlorophenyl)-N-isopropyl-3-(3-methoxypropoxy)propan-1-amine

HRID 426048Notes

Reaction equation

HRID 426048 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([O:22][CH2:23][CH2:24][CH2:25][O:26][CH3:27])[CH2:9][CH2:10][N:11]([CH:19]([CH3:21])[CH3:20])C(=O)OC(C)(C)C)[CH:5]=[CH:6][CH:7]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([O:22][CH2:23][CH2:24][CH2:25][O:26][CH3:27])[CH2:9][CH2:10][NH:11][CH:19]([CH3:20])[CH3:21])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 66704397Tert-butyl 3-(3-chlorophenyl)-3-(3-methoxypropoxy)propyl(isopropyl)carbamate

Product 1

HCID 593643613-(3-chlorophenyl)-N-isopropyl-3-(3-methoxypropoxy)propan-1-amine

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

tert-butyl 3-(3-chlorophenyl)-3-(3-methoxypropoxy)propyl(isopropyl)carbamate was dissolved in a solution of 20% (V/V) TFA/CH2Cl2 (10 mL) and allowed to stir for 1 hour. The solvent and reagent were evaporated before re-dissolving in CH2Cl2 and washing with NaHCO3 saturated solution. The crude 3-(3-chlorophenyl)-N-isopropyl-3-(3-methoxypropoxy)propan-1-amine was isolated (138 mg) and used as is. MS ESI+ve m/z 299 (M+).

Workup

  1. customThe solvent and reagent were evaporated
  2. dissolutionbefore re-dissolving in CH2Cl2
  3. washwashing with NaHCO3 saturated solution

Sources & evidence

ORD record
ord-84ada35b1772428f9256acec7af45064
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

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