Ethylamine → N-{[(2S)-8-fluoro-2,3-dihydro-1,4-benzodioxin-2-yl]methyl}ethanamine

HRID 39020Notes

Reaction equation

HRID 39020 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]2[O:18][C:17]3[C:19]([F:23])=[CH:20][CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=O)=O)=CC=1.[CH2:24]([NH2:26])[CH3:25].C(#N)C>C(CC(C)(C)C)(C)C.CCOC(C)=O.CO>[F:23][C:19]1[C:17]2[O:18][C@@H:13]([CH2:12][NH:26][CH2:24][CH3:25])[CH2:14][O:15][C:16]=2[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 6341EthylamineHCID 6342AcetonitrileHCID 10759436(2R)-8-Fluoro-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl 4-methylbenzenesulfonate

Product 1

HCID 66878480N-{[(2S)-8-fluoro-2,3-dihydro-1,4-benzodioxin-2-yl]methyl}ethanamine

Reagents, catalysts & solvents 1

HCID 19892622HCID 19892622, compoundSolvent

Procedure

Preparation according to Example 5 using [(2R)-8-fluoro-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (4.0 g, 11.8 mmol), ethanamine (5 ml, 70% in water) and ACN (10 ml). Flash column chromatography (Isooctane/EtOAc/MeOH) yielded 2.0 g of the title compound. MS m/z (rel. intensity, 70 eV) 211 (M+, 17), 70 (10), 59 (4), 58 (bp), 56 (4).

Workup

  1. customPreparation

Sources & evidence

ORD record
ord-00be75d02b46454f89e3b517a218cc70
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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