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

HRID 902314ノート

反応式

HRID 902314 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 3776Isopropanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9f2bdd1574dc4badbbaa596d94e9702b
出典データセット
uspto-grants-2008_04
特許番号
US07365095B2

反応ノート

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