Hydrochloric Acid → β-Amino-4-chlorobenzenepropanamide

HRID 423115Notes

Reaction equation

HRID 423115 reaction equation
Cl.O1CCOCC1.[NH2:8][C:9](=[O:27])[CH2:10][CH:11]([NH:19]C(=O)OC(C)(C)C)[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1>C(Cl)Cl>[NH2:19][CH:11]([C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=1)[CH2:10][C:9]([NH2:8])=[O:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 57750339HCID 57750339, compound2×

Product 1

HCID 43147960β-Amino-4-chlorobenzenepropanamideYield 34.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

HCl (4M) in 1,4 dioxane (1.674 mL, 6.69 mmol) was added to tert-butyl 3-amino-1-(4-chlorophenyl)-3-oxopropylcarbamate (Intermediate 106) (200 mg, 0.67 mmol) in DCM (20 mL) at 20° C. The resulting solution was stirred at 20° C. for 4 hours. The reaction mixture was evaporated and was 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 3-amino-3-(4-chlorophenyl)propanamide (46.0 mg, 34.6%) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-eafdd62f27c64ee8bdb943e39b5987c8
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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