Hydrochloric Acid → {1-[3-(1-Amino-ethyl)-phenyl]-pyrrolidin-3-yl}-dimethyl-amine

HRID 857020Notes

Reaction equation

HRID 857020 reaction equation
C(OC(=O)[NH:7][CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]2[CH2:20][CH2:19][CH:18]([N:21]([CH3:23])[CH3:22])[CH2:17]2)[CH:11]=1)[CH3:9])(C)(C)C.Cl>C(OCC)(=O)C>[NH2:7][CH:8]([C:10]1[CH:11]=[C:12]([N:16]2[CH2:20][CH2:19][CH:18]([N:21]([CH3:22])[CH3:23])[CH2:17]2)[CH:13]=[CH:14][CH:15]=1)[CH3:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69588726{1-[3-(3-Dimethylamino-pyrrolidin-1-yl)-phenyl]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 21864685{1-[3-(1-Amino-ethyl)-phenyl]-pyrrolidin-3-yl}-dimethyl-amineYield 99.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of {1-[3-(3-dimethylamino-pyrrolidin-1-yl)-phenyl]-ethyl}-carbamic acid tert-butyl ester (1.8 g) and 4 ml of 4 N HCl in ethyl acetate (10 mL) at 50° C. was stirred for 2 h. After concentration, the residue was neutralized with 10 N NaOH and extracted with methylene chloride. The organic layer was washed with brine, dried over Na2SO4, and concentrated to give the crude product (1.25 g) as an oil.

Workup

  1. concentrationAfter concentration
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7d1febe87c3e4c24a430ef9f115c547a
Source dataset
uspto-grants-2006_12
Patent number
US07144881B2

Reaction notes

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