1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 58080406, compound

HRID 1024504Notes

Reaction equation

HRID 1024504 reaction equation
[Cl:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][CH2:11][O:12][C:6]=2[CH:5]=[C:4]([CH2:13][NH:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH:3]=1.C(OC([N:26]1[CH2:31][CH2:30][N:29]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:28][CH:27]1[C:39](O)=[O:40])=O)(C)(C)C.Cl.C(N=C=NCCCN(C)C)C.CC1C=CN=C(N)C=1C>ClCCl.O>[CH2:32]([N:29]1[CH2:30][CH2:31][NH:26][CH:27]([C:39]([N:14]([CH2:13][C:4]2[CH:3]=[C:2]([Cl:1])[C:7]3[O:8][CH2:9][CH2:10][CH2:11][O:12][C:6]=3[CH:5]=2)[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:40])[CH2:28]1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 110078842-Amino-3,4-dimethylpyridineHCID 16243838HCID 16243838, compoundHCID 43087680N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amine

Product 1

HCID 58080406HCID 58080406, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The mixture of N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amine (84 mg), 4-benzyl-piperazine-1,2-dicarboxylic acid 1-tert-butyl ester (100 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (90 mg), and dimethyl aminopyridine (53 mg) in dichloromethane (8 ml) was stirred at room temperature overnight. After addition of water (8 ml) the reaction mixture was extracted with ethyl acetate (8 ml×3). The organic layers were combined, washed with saturated sodium bicarbonate, water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography on silica (20% ethyl acetate in hexane) to give a resin: MS (m+1)=572.4.

Workup

  1. extractionwas extracted with ethyl acetate (8 ml×3)
  2. washwashed with saturated sodium bicarbonate, water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica (20% ethyl acetate in hexane)
  6. customto give a resin

Sources & evidence

ORD record
ord-32b22fee01d542e3b563a2f596b4503b
Source dataset
uspto-grants-2014_05
Patent number
US08722896B2

Reaction notes

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