Hydrochloric Acid → {4-[4-(2-Aminoethoxy)phenyl]butyl}carbamic acid benzyl ester hydrochloride

HRID 81325Notes

Reaction equation

HRID 81325 reaction equation
[CH2:1]([O:8][C:9](=[O:32])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][NH:24]C(OC(C)(C)C)=O)=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:33].CCOCC>CO.C1COCC1>[ClH:33].[CH2:1]([O:8][C:9](=[O:32])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][NH2:24])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 67364654{4-[4-(2-tert-Butoxycarbonylaminoethoxy)phenyl]butyl}carbamic acid benzyl ester

Product 1

HCID 66849606{4-[4-(2-Aminoethoxy)phenyl]butyl}carbamic acid benzyl ester hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

{4-[4-(2-tert-Butoxycarbonylaminoethoxy)phenyl]butyl}carbamic acid benzyl ester 1 (11.0 g, 24.9 mmol) was dissolved in methanol (110 mL) and THF (20 mL). 12N Hydrochloric acid (40 mL) was added dropwise, and the reaction was allowed to stir. After 1.5 h, ether (200 mL) was added, and the reaction was suction filtered to collect a white solid. The solid was washed with ether, air dried, and dried under vacuum. This afforded 7.6 g, (82%) of 7 as a white solid. 1H NMR (300 MHz, CD3OD) δ 1.39 (br s, 11H), 1.52 (m, 2H),

Workup

  1. filtrationfiltered
  2. customto collect a white solid
  3. washThe solid was washed with ether, air
  4. customdried
  5. customdried under vacuum

Sources & evidence

ORD record
ord-bc0af1aee9554cd6a1fa3fff2feb53ed
Source dataset
uspto-grants-2014_09
Patent number
US08846688B2

Reaction notes

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