1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 68528853, compound

HRID 884095Notes

Reaction equation

HRID 884095 reaction equation
[CH2:1]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]([OH:20])=O)[CH2:13][CH2:12]1)[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[N+:44]([C:47]1[CH:48]=[CH:49][C:50]([O:53][C:54]2[CH:59]=[CH:58][C:57]([NH2:60])=[CH:56][CH:55]=2)=[N:51][CH:52]=1)([O-:46])=[O:45]>CN(C=O)C>[N+:44]([C:47]1[CH:48]=[CH:49][C:50]([O:53][C:54]2[CH:59]=[CH:58][C:57]([NH:60][C:18](=[O:20])[CH2:17][N:14]3[CH2:13][CH2:12][N:11]([CH2:1][C:2]4[CH:10]=[CH:9][C:8]5[O:7][CH2:6][O:5][C:4]=5[CH:3]=4)[CH2:16][CH2:15]3)=[CH:56][CH:55]=2)=[N:51][CH:52]=1)([O-:46])=[O:45]

Participants

6

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 17221251HCID 17221251, compoundHCID 54909083HCID 54909083, compound

Product 1

HCID 68528853HCID 68528853, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (4-piperonylpiperazin-1-yl)acetic acid (13.9 g, 50 mmol) was suspended in DMF (400 mL), and to the resulting suspension were added 1-hydroxybenzotriazole monohydrate (8.42 g, 55 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (10.5 g, 55 mmol) and 4-(5-nitropyridin-2-yloxy)phenylamine (11.6 g, 50 mmol) under ice cooling. The resulting solution was stirred for 6 hours at room temperature. The reaction solution was concentrated under reduced pressure. To the residue was added ethyl acetate, and washed with a saturated sodium bicarbonate solution and brine. The organic layer was left for standing overnight at room temperature, and the resulting precipitated crystals were collected by suction filtration, to thereby yield 12.8 g of the title compound.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionTo the residue was added ethyl acetate
  3. washwashed with a saturated sodium bicarbonate solution and brine
  4. waitThe organic layer was left
  5. waitfor standing overnight at room temperature
  6. customthe resulting precipitated crystals
  7. filtrationwere collected by suction filtration

Sources & evidence

ORD record
ord-87d78767926c4e329146fd3f5bf29124
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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