2-Chloropyrimidine → trans-4-[(Phenylmethyl)amino]-1-[2-(2-pyrimidinylamino)ethyl]-3-piperidinol

HRID 654175Notes

Reaction equation

HRID 654175 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][C@@H:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@H:6]([OH:18])[CH2:5]1.Cl[C:20]1[N:25]=[CH:24][CH:23]=[CH:22][N:21]=1.C(=O)([O-])O.[Na+]>C(O)C>[C:12]1([CH2:11][NH:10][C@@H:7]2[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][NH:1][C:20]3[N:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[CH2:5][C@H:6]2[OH:18])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 744042-ChloropyrimidineHCID 516892Sodium BicarbonateHCID 67833560trans-1-(2-Aminoethyl)-4-[(phenylmethyl)amino]-3-piperidinol

Product 1

HCID 14854947trans-4-[(Phenylmethyl)amino]-1-[2-(2-pyrimidinylamino)ethyl]-3-piperidinolYield 80.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 11.2 parts of trans-1-(2-aminoethyl)-4-[(phenylmethyl)amino]-3-piperidinol in 135 parts of ethanol were added 5.7 parts of 2-chloropyrimidine. After the addition of 8.4 parts of sodium hydrogen carbonate, stirring was continued overnight at reflux temperature. After evaporation, the residue was taken up in a mixture of dichloromethane and water. The separated organic layer was washed with water, dried, filtered and evaoporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 11.84 parts (80.3%) of trans-4-[(phenylmethyl)amino]-1-[2-(2-pyrimidinylamino)-ethyl]-3-piperidinol; mp. 126.9° C. (interm. 18).

Workup

  1. temperatureat reflux temperature
  2. customAfter evaporation
  3. additionthe residue was taken up in a mixture of dichloromethane and water
  4. washThe separated organic layer was washed with water
  5. customdried
  6. filtrationfiltered
  7. customThe residue was crystallized from acetonitrile
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-35f150c126824160988f22548d646a6f
Source dataset
uspto-grants-1992_07
Patent number
US05130312

Reaction notes

Loading…