Hydrochloric Acid → 2-Amino-3-(4-fluorophenyl)propanenitrile hydrochloride

HRID 80686Notes

Reaction equation

HRID 80686 reaction equation
C1(C(=[N:14][CH:15]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:16]#[N:17])C2C=CC=CC=2)C=CC=CC=1.[ClH:26].O>C1COCC1>[ClH:26].[NH2:14][CH:15]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=1)[C:16]#[N:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 584589102-(Diphenylmethyleneamino)-3-(4-fluorophenyl)propanenitrile

Product 1

HCID 671165772-Amino-3-(4-fluorophenyl)propanenitrile hydrochlorideYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(diphenylmethyleneamino)-3-(4-fluorophenyl)propanenitrile, intermediate 1 (1.65 g, 5.02 mmol, 1.0 equiv) in THF (20.1 mL) was added HCl (5.53 mL of a 1 M aqueous solution, 5.53 mmol, 1.1 equiv). After stirring 3 h, the reaction was poured into water and washed with ether (×3). The aqueous layer was neutralized by the addition of 10 M NaOH and extracted with CH2Cl2 (×3). The combined CH2Cl2 extracts were dried (Na2SO4) and then concentrated in vacuo to provide the title compound (0.77 g, 93% yield) as a colorless oil. For convenience, the amine could be converted into the hydrochloride salt by dissolution in ether, treating with 2 M HCl in ether, and filtering the resulting white solid: 1H NMR (400 MHz, CDCl3) δ ppm 7.24-7.29 (m, 2H), 7.01-7.08 (m, 2H), 3.85-3.96 (m, 1H), 2.92-3.07 (m, 2H), 1.60 (d, J=7.55 Hz, 2H).

Workup

  1. washwashed with ether (×3)
  2. additionThe aqueous layer was neutralized by the addition of 10 M NaOH
  3. extractionextracted with CH2Cl2 (×3)
  4. dry with materialThe combined CH2Cl2 extracts were dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9c8712bbbcf44dd88563b389ea070505
Source dataset
uspto-grants-2014_09
Patent number
US08846659B2

Reaction notes

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