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

HRID 902314Notes

Reaction equation

HRID 902314 reaction equation
[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

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9f2bdd1574dc4badbbaa596d94e9702b
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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