Triethylamine → HCID 10849657, compound

HRID 1831002Notes

Reaction equation

HRID 1831002 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH2:18]([O:25][C:26](Cl)=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OCC)(=O)C>ClCCl>[CH2:18]([O:25][C:26](=[O:27])[NH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 683151,4-Benzenedimethanamine

Product 1

HCID 10849657HCID 10849657, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1,4-bis(aminomethyl)benzene (10.0 g, 74 mmol) and triethylamine (9.8 ml, 74 mmol) in dichloromethane (480 ml) was cooled to 0° C. and treated with a solution of benzylchloroformate (10.5 ml, 74 mmol) in dichloromethane (250 ml). The resulting mixture was allowed to warm gradually to room temperature of a period of 16 h. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (450 ml) and 1M aqueous sodium hydroxide (300 ml). The resulting biphasic mixture was filtered and the organic phase separated, dried (magnesium sulfate) and reduced in vacuo to give a waxy solid. Trituration with hot ethyl acetate followed by concentration of the liquors gave the title compound as a waxy solid (7.4 g).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between ethyl acetate (450 ml) and 1M aqueous sodium hydroxide (300 ml)
  3. filtrationThe resulting biphasic mixture was filtered
  4. customthe organic phase separated
  5. dry with materialdried (magnesium sulfate)
  6. customto give a waxy solid

Sources & evidence

ORD record
ord-9ae16fbe9f414f30aba5621774c8c2aa
Source dataset
uspto-grants-2006_06
Patent number
US07067541B2

Reaction notes

Loading…