1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 59970767, compound

HRID 380532Notes

Reaction equation

HRID 380532 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH:15]([OH:23])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]1([C@H:30]([CH3:34])[C:31](O)=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH:15]([O:23][C:31](=[O:32])[C@H:30]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH3:34])[CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27246222-Phenylpropionic acid, (+)-HCID 183647871-Benzyl-4-(3-phenyl-2-hydroxypropyl)piperidine

Product 1

HCID 59970767HCID 59970767, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1 g (3.23 mmol) of 1-benzyl-4-(3-phenyl-2-hydroxypropyl)piperidine (Example 228, Step 2) and 0.775 g (5.16 mmol) of (S)-2-phenylpropionic acid in 10 mL of CH2Cl2 at 0° C. was added 1.32 g (6.9 mmol) of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride and 0.1 g of 4-(dimethylamino)pyridine. The reaction was stirred for 5 h and let warm to rt. To the reaction mixture was added 80 mL of CH2Cl2 and the mixture was washed three times with 10% NaOH solution. The organic layer was washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ethyl acetate, 4:1) to give isomer 1a of the the title compound. Mass Spectrum (ESI) m/e=442 (M+1). [α]D=−3.7 (c=2.44, CHCl3).

Workup

  1. washthe mixture was washed three times with 10% NaOH solution
  2. washThe organic layer was washed with sat'd NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by chromatography (silica, hexanes:ethyl acetate, 4:1)

Sources & evidence

ORD record
ord-c3d1f61766b34d54bddfaa9103bbab75
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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