Benzyl Chloride → N2,N4,N4-trimethyl-N2-[1-(phenylmethyl)-4-piperidinyl]-2,4-pyrimidinediamine

HRID 1937415Notes

Reaction equation

HRID 1937415 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:9][N:10]([CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)[C:11]1[N:16]=[C:15]([N:17]([CH3:19])[CH3:18])[CH:14]=[CH:13][N:12]=1.C(N(CC)CC)C>CN(C)C(=O)C>[CH3:9][N:10]([CH:20]1[CH2:25][CH2:24][N:23]([CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:22][CH2:21]1)[C:11]1[N:16]=[C:15]([N:17]([CH3:18])[CH3:19])[CH:14]=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 8471TriethylamineHCID 53854017N2,N4,N4-trimethyl-N2-(4-piperidinyl)-2,4-pyrimidinediamine

Product 1

HCID 57066986N2,N4,N4-trimethyl-N2-[1-(phenylmethyl)-4-piperidinyl]-2,4-pyrimidinediamineYield 55.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of chloromethylbenzene (1.9 g), intermediate 2 (3 g) and triethylamine (2.62 g) in N,N-dimethylacetamide (55 ml) was stirred for 2 hours at 75° C. The reaction mixture was poured out into ice-water and extracted with toluene. The separated organic layer was washed three times with water, dried, filtered and the solvent evaporated. The residue was dissolved in boiling petroleum ether and treated with activated charcoal. The mixture was filtered warm over dicalite, and the filtrate was concentrated. The concentrate was cooled on an ice-bath and the resulting precipitate was filtered off and dried, yielding 2.3 g (54.4%) of N2,N4,N4-trimethyl-N2-[1-(phenylmethyl)-4-piperidinyl]-2,4-pyrimidinediamine (comp. 8).

Workup

  1. extractionextracted with toluene
  2. washThe separated organic layer was washed three times with water
  3. customdried
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. dissolutionThe residue was dissolved
  7. additiontreated with activated charcoal
  8. filtrationThe mixture was filtered
  9. temperaturewarm over dicalite
  10. concentrationthe filtrate was concentrated
  11. temperatureThe concentrate was cooled on an ice-bath
  12. filtrationthe resulting precipitate was filtered off
  13. customdried

Sources & evidence

ORD record
ord-39e5f7c0c7a04a6b8f610113f81985dc
Source dataset
uspto-grants-2002_05
Patent number
US06395742B1

Reaction notes

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