2-Chlorobenzaldehyde → 1-(2-Chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

HRID 1797932노트

반응식

HRID 1797932 반응식
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH2:20][CH2:21][NH2:22])[CH:15]=[CH:16][C:17]=1[O:18][CH3:19]>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[C:15]2[C:14](=[CH:13][C:12]([O:11][CH3:10])=[C:17]([O:18][CH3:19])[CH:16]=2)[CH2:20][CH2:21][NH:22]1

참가 물질

4

반응물 2

HCID 69962-ChlorobenzaldehydeHCID 8421Homoveratrylamine

생성물 1

HCID 31584181-(2-Chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

To a mixture of 2-chlorobenzaldehyde (0.5 M in dichloromethane) (800 μl) and 2-(3,4-dimethoxy-phenyl)-ethylamine (0.25 M in dichloromethane) (800 μl) was added trifluoroacetic acid (150 μl). The mixture was shaken at room temperature for 12-24 hours then evaporated to dryness. Toluene (1 ml) was added the mixture vortexed and re-evaporated to dryness. The residue was dissolved in methanol (1.5 ml) and dichloromethane (1 ml) and filtered through a SCX cartridge (Bakerbond JT7090-07, aromatic sulfonic acid). The cartridge was washed with methanol (3 ml) the product eluted with 0.5 M ammonia solution (5 ml). Product containing fractions were combined and evaporated to dryness. Toluene (1 ml) was added the mixture vortexed and re-evaporated to dryness to give 1-(2-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline which was used directly in the next step.

후처리

  1. customthen evaporated to dryness
  2. additionToluene (1 ml) was added the mixture
  3. customre-evaporated to dryness
  4. dissolutionThe residue was dissolved in methanol (1.5 ml)
  5. filtrationdichloromethane (1 ml) and filtered through a SCX cartridge (Bakerbond JT7090-07, aromatic sulfonic acid)
  6. washThe cartridge was washed with methanol (3 ml) the product
  7. washeluted with 0.5 M ammonia solution (5 ml)
  8. additionProduct containing fractions
  9. customevaporated to dryness
  10. additionToluene (1 ml) was added the mixture
  11. customre-evaporated to dryness

출처 및 근거

ORD 기록
ord-2af2c301f8a948af88608ea1a6f7ed04
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343961B2

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