Benzylamine → HCID 3494033, compound

HRID 1589828Notes

Reaction equation

HRID 1589828 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH2:12]([NH2:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:12]([NH:19][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 10340Sodium CarbonateHCID 140539Isoquinoline, 1-chloro-

Product 1

HCID 3494033HCID 3494033, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Chloroisoquinoline (1.64 g, 0.01 mol) and benzylamine (2.14 g, 0.02 mol) were mixed at room temperature and heated, with stirring, in an oil-bath at 50° for 4 hours. The mixture was cooled to give a crystalline solid which was equilibrated between methylene chloride (CH2Cl2) and aqueous Na2CO3. The CH2Cl2 fraction was washed with water, dried and evaporated to dryness to give an oil which crystallised on standing (3.0 g). This material was twice re-crystallised from ether/40-60 petroleum ether to give the title compound as buff crystals, m.p. 101°-102°.

Workup

  1. temperatureheated
  2. temperatureThe mixture was cooled
  3. customto give a crystalline solid which
  4. washThe CH2Cl2 fraction was washed with water
  5. customdried
  6. customevaporated to dryness
  7. customto give an oil which
  8. customcrystallised
  9. customThis material was twice re-crystallised from ether/40-60 petroleum ether

Sources & evidence

ORD record
ord-3d27278a89eb4b2eae184250c8402bc5
Source dataset
uspto-grants-1993_04
Patent number
US05200417

Reaction notes

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