Trifluoroacetic acid → N-(3-amino-3-(4-chlorophenyl)propyl)acetamide

HRID 423047Notes

Reaction equation

HRID 423047 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH:7]([NH:15]C(=O)OC(C)(C)C)[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O>>[NH2:15][CH:7]([C:8]1[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=1)[CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57750301Tert-butyl 3-acetamido-1-(4-chlorophenyl)propylcarbamate2×

Product 1

HCID 57750409N-(3-amino-3-(4-chlorophenyl)propyl)acetamideYield 40%

Conditions

Temperature
20 °C

Procedure

tert-Butyl 3-acetamido-1-(4-chlorophenyl)propylcarbamate (Intermediate 26) (142 mg, 0.43 mmol) was added to TFA (2 mL) at 20° C. The resulting solution was stirred at 20° C. for 40 minutes. The reaction mixture was evaporated and purified by ion exchange chromatography using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and pure fractions were evaporated to dryness to afford N-(3-amino-3-(4-chlorophenyl)propyl)acetamide (39.0 mg, 39.6%) as a colourless gum. m/z (ESI+) (M+H)+=227; HPLC tR=1.32 min.

Workup

  1. customThe reaction mixture was evaporated
  2. custompurified by ion exchange chromatography
  3. washThe desired product was eluted from the column
  4. customwere evaporated to dryness

Sources & evidence

ORD record
ord-79da7c2e3cb34cf6b05c4113edd926df
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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