(S)-1-(2-Fluorophenyl)ethylamine → HCID 178462016, compound

HRID 2369957Notes

Reaction equation

HRID 2369957 reaction equation
[CH3:1][C:2]1([CH3:22])[C:7]([CH3:9])([CH3:8])[O:6][C:5](OC2C=CC([N+]([O-])=O)=CC=2)=[N:4][S:3]1(=[O:21])=[O:20].[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C@@H:30]([NH2:32])[CH3:31]>ClCCl.C(N(CC)C(C)C)(C)C>[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C@@H:30]([NH:32][C:5]1[O:6][C:7]([CH3:8])([CH3:9])[C:2]([CH3:1])([CH3:22])[S:3](=[O:20])(=[O:21])[N:4]=1)[CH3:31]

Participants

5

Reactant 2

HCID 7023579(S)-1-(2-Fluorophenyl)ethylamineHCID 718136815,5,6,6-Tetramethyl-2-(4-nitrophenoxy)-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide

Product 1

HCID 178462016HCID 178462016, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

200 mg of 5,5,6,6-tetramethyl-2-(4-nitrophenoxy)-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide and 111 mg of (S)-1-(2-fluorophenyl)ethylamine were dissolved in 1 ml of dichloromethane and 0.10 ml of N,N-diisopropylethylamine, and the mixture was stirred at room temperature for 16 hours. Subsequently, the reaction solution was diluted with 50 ml of dichloromethane, washed three times with 30 ml of 10% aqueous ammonia solution, three times with 30 ml of 1 N aqueous hydrochloric acid and with 30 ml of saturated aqueous sodium hydrogencarbonate solution, dried over Na2SO4 and concentrated by rotary evaporation. This gave the product (194 mg) with a molecular weight of 328.4 g/mol (C15H21FN2O3S); MS (ESI): m/e=329 (M+H+).

Workup

  1. washwashed three times with 30 ml of 10% aqueous ammonia solution, three times with 30 ml of 1 N aqueous hydrochloric acid
  2. dry with materialwith 30 ml of saturated aqueous sodium hydrogencarbonate solution, dried over Na2SO4
  3. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-afea6a501c1e4522be3820473a3f8920
Source dataset
uspto-grants-2014_04
Patent number
US08710050B2

Reaction notes

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