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Hydrochloric Acid → N-(4-fluorobenzyl)-N-[(trans)-2-phenylcyclopropyl]amine hydrochloride

HRID 882334
Notes
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Reaction equation

HRID 882334 reaction equation
[ClH:1].[F:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][NH:8][C@@H:9]2[CH2:11][C@H:10]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][CH:4]=1>CCOCC>[ClH:1].[F:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C@@H:9]2[CH2:11][C@H:10]2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:18][CH:19]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 46869734N-(4-fluorobenzyl)-N-[(trans)-2-phenylcyclopropyl]amine

Product 1

HCID 66629772N-(4-fluorobenzyl)-N-[(trans)-2-phenylcyclopropyl]amine hydrochlorideYield 83.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

2 M ethereal solution of HCl (0.24 mL, 0.47 mmol) was slowly added to a solution of N-(4-fluorobenzyl)-N-[(trans)-2-phenylcyclopropyl]amine (95 mg, 0.39 mmol) in dry Et2O (10 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 90 mg of N-(4-fluorobenzyl)-N-[(trans)-2-phenylcyclopropyl]amine hydrochloride (white solid, 83% yield).

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-b0bbc109f1064c8ebe29c3111d58e128
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08993808B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes