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Hydrochloric Acid → Methyl 4-(2-aminoethyl)benzoate hydrochloride

HRID 2305231
Notes
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Reaction equation

HRID 2305231 reaction equation
C(OC([NH:8][CH2:9][CH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)=O)(C)(C)C.[ClH:21]>C(Cl)Cl.O1CCOCC1>[ClH:21].[NH2:8][CH2:9][CH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22710013Methyl 4-[2-(tert-butoxycarbonylamino)ethyl]benzoate

Product 1

HCID 13078671Methyl 4-(2-aminoethyl)benzoate hydrochlorideYield 97%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes

To a solution of methyl 4-[2-(tert-butoxycarbonylamino)ethyl]benzoate (3.50 g, 12.5 mmol) in methylene chloride (35 ml) was added 4N hydrogen chloride in 1,4-dioxane (35 ml) at 5° C. and the mixture was stirred for 30 min. The solvent was removed in vacuo and the resulting solid was collected, washed with isopropyl ether and dried to give methyl 4-(2-aminoethyl)-benzoate hydrochloride (2.63 g, 97%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe resulting solid was collected
  3. washwashed with isopropyl ether
  4. customdried

Sources & evidence

ORD record
ord-d397bffb15f24cf88398ef427fe05ee3
Source dataset
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06437146B1

Reaction notes

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