Hydrochloric Acid → HCID 66629893, compound

HRID 882338Notes

Reaction equation

HRID 882338 reaction equation
[ClH:1].[C:2]1([C@@H:8]2[CH2:10][C@H:9]2[NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOCC>[ClH:1].[C:2]1([C@@H:8]2[CH2:10][C@H:9]2[NH:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:17][CH:18]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 46869801HCID 46869801, compound

Product 1

HCID 66629893HCID 66629893, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

2 M ethereal solution of HCl (0.28 mL, 0.57 mmol) was slowly added to a solution of N-[(trans)-2-phenylcyclopropyl]-N-[4-(trifluoromethyl)benzyl]amine (150 mg, 0.51 mmol) in dry Et2O (8 mL) cooled at −78° C., and allowed to reach room temperature. After 10 min the white precipitate was allowed to settle and Et2O was decanted, the solid was washed with Et2O (10 mL) and vacuum dried, rendering 105 mg of N-[(trans)-2-phenylcyclopropyl]-N-[4-(trifluoromethyl)benzyl]amine hydrochloride (white solid, 62% yield). 1H-NMR (MeOD, 250 MHz, δ): 7.78-7.65 (m, 4H, ArH); 7.34-7.20 (m, 3H, ArH); 7.13-7.06 (m, 2H, ArH); 4.49 (s, 2H, CH2); 3.07-2.97 (m, 1H, CH); 2.51-2.40 (m, 1H, CH); 1.61-1.49 (m, 1H, CH2); 1.46-1.34 (m, 1H, CH2).

Workup

  1. customto reach room temperature
  2. customEt2O was decanted
  3. washthe solid was washed with Et2O (10 mL) and vacuum
  4. customdried

Sources & evidence

ORD record
ord-8e51d68bc28c4eb3b15081ddfc5aea67
Source dataset
uspto-grants-2015_03
Patent number
US08993808B2

Reaction notes

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