Benzenemethanol, 4-amino-alpha-(aminomethyl)-3,5-dichloro- → HCID 13920697, compound

HRID 1084967Notes

Reaction equation

HRID 1084967 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([NH2:21])=[O:20])=[CH:14][CH:13]=1.[NH2:22][C:23]1[C:28]([Cl:29])=[CH:27][C:26]([CH:30]([CH2:32][NH2:33])[OH:31])=[CH:25][C:24]=1[Cl:34]>CN(C=O)C>[NH2:22][C:23]1[C:24]([Cl:34])=[CH:25][C:26]([CH:30]([OH:31])[CH2:32][NH:33][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]([NH2:21])=[O:20])=[CH:14][CH:13]=2)=[CH:27][C:28]=1[Cl:29]

Participants

4

Reactant 2

HCID 217242Benzenemethanol, 4-amino-alpha-(aminomethyl)-3,5-dichloro-HCID 13920684HCID 13920684, compound

Product 1

HCID 13920697HCID 13920697, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[3-[(6-Bromohexyl)oxy]propyl]benzeneacetamide (950 mg) was added to a stirred solution of 4-amino-α-(aminomethyl)-3,5-dichloro-benzenemethanol (900 mg) and DEA (650 mg) in DMF (10 ml) at 100° under nitrogen. After 1 h the solvent was evaporated and the residue was partitioned between 8% sodium bicarbonate (20 ml) and ethyl acetate (20 ml). The organic layer was washed with water and brine, dried and concentrated in vacuo to give a yellow solid which was triturated with ether to give the title compound as an off-white powder (510 mg) m.p. 104°-106°.

Workup

  1. customAfter 1 h the solvent was evaporated
  2. customthe residue was partitioned between 8% sodium bicarbonate (20 ml) and ethyl acetate (20 ml)
  3. washThe organic layer was washed with water and brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customto give a yellow solid which
  7. customwas triturated with ether

Sources & evidence

ORD record
ord-88a4e15e37e7488f81f647df68443231
Source dataset
uspto-grants-1991_04
Patent number
US05006556

Reaction notes

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