Hydrochloric Acid → 4-(Dibenzylamino)butanoic acid

HRID 473604Notes

Reaction equation

HRID 473604 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][CH2:6][CH2:7][N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)C.Cl>C1COCC1>[CH2:16]([N:8]([CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:7][CH2:6][CH2:5][C:4]([OH:23])=[O:3])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13929784Ethyl 4-(Dibenzylamino)butanoate

Product 1

HCID 146277764-(Dibenzylamino)butanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 500 mg (1.6 mmol, 1 equiv.) of 4-dibenzylamino-butyric acid ethyl ester in 1 ml of THF was added 4 ml of HCl 2N and the resulting mixture was stirred for 48 hours. After decantation and separation, the aqueous layer was extracted twice by ethyl acetate. The pH was fixed to 5 using solid sodium carbonate and the aqueous layer was extracted by dichloromethane. The dichloromethane layer was dried over sodium sulphate, evaporated and used without further purification.

Workup

  1. customAfter decantation and separation
  2. extractionthe aqueous layer was extracted twice by ethyl acetate
  3. extractionthe aqueous layer was extracted by dichloromethane
  4. dry with materialThe dichloromethane layer was dried over sodium sulphate
  5. customevaporated
  6. customused without further purification

Sources & evidence

ORD record
ord-592d667beef04324878fc26cb879470e
Source dataset
uspto-grants-2014_01
Patent number
US08637496B2

Reaction notes

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