Hydrochloric Acid → 3-Amino-3-(4-chlorophenyl)propanenitrile

HRID 423121Notes

Reaction equation

HRID 423121 reaction equation
Cl.O1CCOCC1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([NH:19]C(=O)OC(C)(C)C)[CH2:16][C:17]#[N:18])=[CH:11][CH:10]=1>C(Cl)Cl>[NH2:19][CH:15]([C:12]1[CH:11]=[CH:10][C:9]([Cl:8])=[CH:14][CH:13]=1)[CH2:16][C:17]#[N:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 57750327Tert-butyl 1-(4-chlorophenyl)-2-cyanoethylcarbamate2×

Product 1

HCID 552833543-Amino-3-(4-chlorophenyl)propanenitrileYield 120.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

HCl (4M) in 1,4-dioxane (0.668 mL, 2.67 mmol) was added in one portion to tert-butyl 1-(4-chlorophenyl)-2-cyanoethylcarbamate (Intermediate 24) (150 mg, 0.53 mmol) in DCM (4 mL) at 20° C. The resulting solution was stirred at 20° C. for 18 hours. The reaction mixture was evaporated to afford 3-amino-3-(4-chlorophenyl)propanenitrile (HCl salt) (115 mg, 99%) as a white solid.

Workup

  1. customThe reaction mixture was evaporated

Sources & evidence

ORD record
ord-b503fb5ad59e4b16b9e907c777db0026
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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