Tetrahydrofuran → 3-[4-(Aminomethyl)-3-fluorophenyl]propylamine dihydrochlorde

HRID 48371Notes

Reaction equation

HRID 48371 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[C:7]([F:13])[CH:6]=1.CSC.[B].C1COCC1.C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:35].Cl>>[ClH:35].[ClH:35].[NH2:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][CH2:3][CH2:2][NH2:1])=[CH:6][C:7]=1[F:13]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 9833925Boron, trihydro(thiobis(methane))-, (T-4)-HCID 227432424-(3-Aminopropyl)-2-fluorobenzenecarbonitrile

Product 1

HCID 227432583-[4-(Aminomethyl)-3-fluorophenyl]propylamine dihydrochlordeYield 73%

Procedure

Scheme IIIb, step C: 4-(3-Aminopropyl)-2-fluorobenzenecarbonitrile (1.1 g, 6.17 mmol) and boron dimethylsulfide 2M in THF (6.2 mL, 12.34 mmol) were combined and reduction was carried out in a manner analogous to the procedure described in example 6 to provide the intermediate title compound, 3-[4-(aminomethyl)-3-fluorophenyl]propylamine dihydrochlorde, (1.15 g, 73%) as a dihydrochloride salt. Electron spray M.S. 183 (M*+H).

Sources & evidence

ORD record
ord-0b9e30f3f7794c1395bfc3dca421aae1
Source dataset
uspto-grants-2004_03
Patent number
US06703425B2

Reaction notes

Loading…