Tert-butyl{1-[3-(4-chloro-2-cyanophenoxy)phenyl]ethyl}carbamate → Hydrochloric Acid

HRID 449521Notes

Reaction equation

HRID 449521 reaction equation
C(OC(=O)[NH:7][CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[C:24]#[N:25])[CH:11]=1)[CH3:9])(C)(C)C>Cl.O1CCOCC1>[NH2:7][CH:8]([C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=1)[O:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[C:24]#[N:25])[CH3:9].[ClH:23]

Participants

5

Reactant 1

HCID 59496674Tert-butyl{1-[3-(4-chloro-2-cyanophenoxy)phenyl]ethyl}carbamate

Product 2

HCID 313Hydrochloric AcidYield 2,300.8%HCID 594966982-[3-(1-Aminoethyl)phenoxy]-5-chlorobenzonitrile

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

The tert-butyl{1-[3-(4-chloro-2-cyanophenoxy)phenyl]ethyl}carbamate (0.040 g) was taken up in 4 M HCl in dioxane (3 mL) at r.t. and was stirred for 2 h. The reaction was concentrated under reduced pressure, taken up in acetonitrile and re-concentrated under reduced pressure two times to give crude 2-[3-(1-aminoethyl)phenoxy]-5-chlorobenzonitrile as HCl salt (0.045 g) as a semisolid residue. Analytical LCMS (M+H)+: m/z=272.9.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. concentrationre-concentrated under reduced pressure two times

Sources & evidence

ORD record
ord-dce03dad004f40eaa83faa1f4a71fe5a
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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