Diisopropylethylamine → N-[2-(chroman-3-yl)ethyl]-N-(2-methoxycarbonylethyl)-amine hydrochloride

HRID 1196040Notes

Reaction equation

HRID 1196040 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][CH:13]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[O:15][CH2:14]2)(=O)=O)=CC=1.[ClH:24].[CH3:25][O:26][C:27]([CH2:29][CH2:30][NH2:31])=[O:28].C(N(C(C)C)C(C)C)C>CN(C)C=O>[ClH:24].[O:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:22][CH:13]([CH2:12][CH2:11][NH:31][CH2:30][CH2:29][C:27]([O:26][CH3:25])=[O:28])[CH2:14]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 148384153-[2-(p-Toluenesulphonyloxy)ethyl]chroman

Product 1

HCID 14838449N-[2-(chroman-3-yl)ethyl]-N-(2-methoxycarbonylethyl)-amine hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

33.2 g (0.1 mol) of 3-[2-(p-toluenesulphonyloxy)ethyl]chroman, 14.0 g of N-(2-methoxycarbonylethyl)-amine hydrochloride and 39 g of N-ethyl-N,N-diisopropylamine are dissolved under nitrogen in 750 ml of dimethylformamide and the solution is stirred for 16 hours at room temperature. The reaction mixture is subsequently concentrated to approximately 200 ml under reduced pressure, 500 ml of water are then added and the whole is extracted by shaking three times with 150 ml of dichloromethane each time. The combined organic phases are dried over sodium sulphate and concentrated to dryness by evaporation. By adding ethanolic hydrochloric acid and cooling, N-[2-(chroman-3-yl)ethyl]-N-(2-methoxycarbonylethyl)-amine hydrochloride having a melting point of 190°-192° is obtained.

Workup

  1. concentrationThe reaction mixture is subsequently concentrated to approximately 200 ml under reduced pressure, 500 ml of water
  2. additionare then added
  3. extractionthe whole is extracted
  4. stirringby shaking three times with 150 ml of dichloromethane each time
  5. dry with materialThe combined organic phases are dried over sodium sulphate
  6. concentrationconcentrated to dryness by evaporation
  7. additionBy adding ethanolic hydrochloric acid
  8. temperaturecooling

Sources & evidence

ORD record
ord-6cba8bbbb3c946f99f93dc2c2ca8cb86
Source dataset
uspto-grants-1992_05
Patent number
US05112855

Reaction notes

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