N,N-Dimethylethylenediamine → HCID 18319613, compound

HRID 1699378Notes

Reaction equation

HRID 1699378 reaction equation
[C:1]([C:4]1[C:14]2[O:13][CH2:12][CH2:11][C:10]([C:15]([O-:17])=[O:16])=[CH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([OH:3])=O.[CH3:18][N:19]([CH3:23])[CH2:20][CH2:21][NH2:22].Cl.CN(C)[CH2:27][CH2:28]CN=C=NCC>ClCCl>[CH3:18][N:19]([CH2:20][CH2:21][NH:22][C:1]([C:4]1[C:14]2[O:13][CH2:12][CH2:11][C:10]([C:15]([O:17][CH2:27][CH3:28])=[O:16])=[CH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)=[O:3])[CH3:23]

Participants

5

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18319603HCID 18319603, compound

Product 1

HCID 18319613HCID 18319613, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 9-carboxy-2,3-dihydro-1-benzoxepin-4-carboxylate (0.39 g), N,N-dimethylethylenediamine (0.163 ml), and 1-hydroxybenzotriaole hydrate (0.22 g) in dichloromethane (8 ml) was added 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride (0.31 g). The reaction mixture was stirred for 4.5 hours at ambient temperature and evaporated in vacuo. The residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was washed successively with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo to give a solid of ethyl 2,3-dihydro-9-[2-(N,N-dimethylamino)-ethylaminocarbonyl]-1-benzoxepin-4-carboxylate (0.39 g),

Workup

  1. customevaporated in vacuo
  2. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  3. washThe organic layer was washed successively with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-40c386411dc84634a49e6d9658252712
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

Loading…