1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 13338740, compound

HRID 2417837Notes

Reaction equation

HRID 2417837 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][CH:11]([N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25])[C:12]([OH:14])=O.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[C:19]1(=[O:20])[N:15]([CH:11]2[CH2:10][CH2:9][CH2:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[NH:1][C:12]2=[O:14])[C:16](=[O:25])[C:17]2=[CH:24][CH:23]=[CH:22][CH:21]=[C:18]12

Participants

4

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13338743HCID 13338743, compound

Product 1

HCID 13338740HCID 13338740, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(2-aminophenyl)-2-phthalimidopentanoic acid (3.5 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.9 g) in dimethylformamide (85 ml) is stirred at room temperature under a nitrogen atmosphere for 65 hours. The solvent is removed under high vacuum and the residue distributed between ethyl acetate (250 ml) and water (150 ml). The organic phase is washed with 2N sodium hydroxide (100 ml) and water (100 ml), and dried over sodium sulfate. The solvent is removed under reduced pressure and the residue recrystallized from methanol/ethyl acetate to give 3-phthalimido-3,4,5,6-tetrahydro-1-benzazocin-2(1H)one, mp 229°-230° C., used without further purification in the next synthetic step.

Workup

  1. customThe solvent is removed under high vacuum
  2. washThe organic phase is washed with 2N sodium hydroxide (100 ml) and water (100 ml)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is removed under reduced pressure
  5. customthe residue recrystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-6e0eeaea9226447c85f9e14fa62f6456
Source dataset
uspto-grants-1984_09
Patent number
US04470988

Reaction notes

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