Trifluoroacetic acid → [4-(4-Aminobutyl)phenoxy]acetonitrile

HRID 132573Notes

Reaction equation

HRID 132573 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]#[N:21])=[CH:14][CH:13]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]#[N:21])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21031133[4-(4-Cyanomethoxyphenyl)butyl]carbamic acid tert-butyl ester

Product 1

HCID 22054440[4-(4-Aminobutyl)phenoxy]acetonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 40 (0.105 g, 0.345 mmol) was dissolved in dichloromethane (10 mL). Trifluoroacetic acid (2 mL) was added in one portion. The mixture was stirred at room temperature for 2 h, and then concentrated under vacuum to dryness. The crude residue was used directly without further purification. 1H NMR (300 MHz, CD3OD): δ 1.60-1.75 (m, 4H), 2.65 (t, 2H), 2.92 (t, 2H), 4.38 (s, 2H), 6.96 (d, 2H), 7.20 (d, 2H). m/z (APCI): 205 [C12H16N2O+H]+.

Workup

  1. concentrationconcentrated under vacuum to dryness
  2. customThe crude residue was used directly without further purification

Sources & evidence

ORD record
ord-e0a2b8de08ac465bb5e71879c017a3a5
Source dataset
uspto-grants-2008_06
Patent number
US07388013B2

Reaction notes

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