1-Butanol → HCID 28530649, compound

HRID 1258143Notes

Reaction equation

HRID 1258143 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[Cl:15][C:16]1[N:17]=[N:18][C:19](Cl)=[CH:20][CH:21]=1.C(O)CCC.O>ClCCl>[CH2:8]([N:5]1[CH2:6][CH2:7][CH:2]([NH:1][C:19]2[N:18]=[N:17][C:16]([Cl:15])=[CH:21][CH:20]=2)[CH2:3][CH2:4]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 962WaterHCID 673313,6-DichloropyridazineHCID 4158521-Benzyl-4-piperidylamine

Product 1

HCID 28530649HCID 28530649, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-amino-1-benzylpiperidine (4 g, 21 mmol) and 3,6-dichloro-pyridazine (1.56 g, 10.5 mmol) was stirred for 1 h at 120° C., before n-butanol (10 ml) was added and the reaction mixture stirred for a further 1 h at 120° C. After addition of water and dichloromethane, the organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The residue was crystallized from acetonitrile and the resulting solid was filtered off and dried to yield D1 (1.3 g, 41%) as a solid. C16H19ClN4 requires 302. Found 303 (MH+); mp: 208.2-209.3° C.

Workup

  1. additionwas added
  2. customthe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customThe residue was crystallized from acetonitrile
  7. filtrationthe resulting solid was filtered off
  8. customdried

Sources & evidence

ORD record
ord-3e895b78de8e4e02ada4d41a0238e64c
Source dataset
uspto-grants-2013_06
Patent number
US08466153B2

Reaction notes

Loading…