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

HRID 1937415노트

반응식

HRID 1937415 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
75 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-39e5f7c0c7a04a6b8f610113f81985dc
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06395742B1

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