Hydrochloric Acid → {[8-(2-chlorophenyl)-6-fluoro-3,4-dihydro-2H-chromen-2-yl]methyl}amine hydrochloride

HRID 902314노트

반응식

HRID 902314 반응식
[N:1]([CH2:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[CH:9]=[C:10]([F:15])[CH:11]=2)[O:6]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)C.Cl>O1CCCC1.O.CC(O)C.CCCCCC>[ClH:22].[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:8]1[CH:9]=[C:10]([F:15])[CH:11]=[C:12]2[C:7]=1[O:6][CH:5]([CH2:4][NH2:1])[CH2:14][CH2:13]2

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 866091102-Azidomethyl-8-(2-chloro-phenyl)-6-fluoro-chroman

생성물 1

HCID 69117794{[8-(2-chlorophenyl)-6-fluoro-3,4-dihydro-2H-chromen-2-yl]methyl}amine hydrochloride수율 134.4%

시약·촉매·용매 4

HCID 962Water용매HCID 3776Isopropanol용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

To a solution of 2-azidomethyl-8-(2-chloro-phenyl)-6-fluoro-chroman (170 mg, 0.535 mmol) in tetrahydrofuran (5 mL) and water (0.5 mL) was added polymer-bound triphenylphosphine (˜3 mmol/g, 0.535 g, 1.605 mmol) and the reaction mixture stirred at room temperature for 24 hours. The brown suspension was then filtered through celite, the filter cake washed with ethyl acetate (50 mL) and the combined filtrates concentrated under reduced pressure to afford a yellow syrup. The product was dissolved in 2-propanol (1 mL) and diethyl ether (2 mL) and a solution of hydrogen chloride (1.0 M in diethyl ether, 0.51 mL, 0.51 mmol) added followed hexane (4 mL). The resulting white precipitate was filtered to afford 118 mg (67%) of {[8-(2-chlorophenyl)-6-fluoro-3,4-dihydro-2H-chromen-2-yl]methyl}amine hydrochloride as a white solid. HRMS: calcd for C16H15ClFNO+H+, 292.08990. found (ESI, [M+H]+), 292.0903.

후처리

  1. filtrationThe brown suspension was then filtered through celite
  2. washthe filter cake washed with ethyl acetate (50 mL)
  3. concentrationthe combined filtrates concentrated under reduced pressure
  4. customto afford a yellow syrup
  5. filtrationThe resulting white precipitate was filtered

출처 및 근거

ORD 기록
ord-9f2bdd1574dc4badbbaa596d94e9702b
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365095B2

반응 노트

불러오는 중…