(1S)-1-(2-chlorophenyl)ethan-1-amine hydrochloride → HCID 178462015, compound

HRID 72365Notes

Reaction equation

HRID 72365 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].Cl.[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C@@H:31]([NH2:33])[CH3:32]>ClCCl.C(N(CC)C(C)C)(C)C>[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C@@H:31]([NH:33][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)[CH3:32]

Participants

5

Reactant 2

HCID 45072355(1S)-1-(2-chlorophenyl)ethan-1-amine hydrochlorideHCID 718136815,5,6,6-Tetramethyl-2-(4-nitrophenoxy)-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide

Product 1

HCID 178462015HCID 178462015, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

Under inert gas, 200 mg of 5,5,6,6-tetramethyl-2-(4-nitrophenoxy)-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide and 176 mg of (S)-1-(2-chlorophenyl)ethylamine hydrochloride were dissolved in 1 ml of dichloromethane and 0.21 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 (171 mg) with a molecular weight of 344.94 g/mol (C15H21ClN2O3S); MS (ESI): m/e=345 (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-58754ac3064f4c19954cdd378618be17
Source dataset
uspto-grants-2014_09
Patent number
US08828994B2

Reaction notes

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