Benzhydrylamine → HCID 20459477, compound

HRID 544128Notes

Reaction equation

HRID 544128 reaction equation
[CH:1]([NH2:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])C.BrC[C:24]1[CH:29]=[CH:28][C:27](CBr)=[CH:26][CH:25]=1>C(#N)C>[C:2]1([CH:1]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:14][CH2:7][C:2]2[CH:3]=[CH:4][C:21]([CH2:20][NH:17][CH:18]([C:19]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:8][CH:1]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7036BenzhydrylamineHCID 8471TriethylamineHCID 693351,4-Bis(bromomethyl)benzene

Product 1

HCID 20459477HCID 20459477, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A mixture of 18.3 g of benzhydrylamine, 10 g of triethylamine and 60 ml of acetonitrile is added dropwise to a boiling mixture of 13.2 g of 1,4-bis-(bromomethyl)-benzene in 60 ml of acetonitrile. The mixture is left to boil overnight, is greatly concentrated, and partitioned between 200 ml of ether and 200 ml of 10% sodium hydroxide solution, concentrated by evaporation and recrystallised from diethyl ether. N,N'-bis-(diphenylmethyl)-p-xylylenediamine having a melting point of 92°-94° C. is obtained.

Workup

  1. waitThe mixture is left
  2. concentrationis greatly concentrated
  3. custompartitioned between 200 ml of ether and 200 ml of 10% sodium hydroxide solution
  4. concentrationconcentrated by evaporation
  5. customrecrystallised from diethyl ether

Sources & evidence

ORD record
ord-05a1761919bb46b2b8e3ad809ad47001
Source dataset
uspto-grants-1984_05
Patent number
US04448776

Reaction notes

Loading…