Gramine → (2,3-dihydro-1H-indol-3-ylmethyl)dimethylamine

HRID 1631666Notes

Reaction equation

HRID 1631666 reaction equation
C([BH3-])#N.[Na+].[CH3:5][N:6]([CH2:8][C:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][CH:10]=1)[CH3:7]>FC(F)(F)C(O)=O>[NH:11]1[C:12]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:9]([CH2:8][N:6]([CH3:7])[CH3:5])[CH2:10]1

Participants

4

Reactant 2

HCID 6890GramineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 13156058(2,3-dihydro-1H-indol-3-ylmethyl)dimethylamineYield 65.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

1.1 g of sodium cyanoborohydride is gradually added to a solution of 1 g of gramine in 20 ml of trifluoroacetic acid, under argon, cooled in an ice bath, and stirred for half an hour at 0° C. and then for 2 h at ambient temperature. The reaction medium is plunged into 50 g of ice and alkalinized using 30% sodium hydroxide, and is then extracted with four times 30 ml of ethyl acetate. The organic phase is washed with 20 ml of water, dried over anhydrous magnesium sulphate, filtered, and then concentrated to dryness under reduced pressure. After a silica column purification, eluent: 85/15 v/v CH2Cl2/MeOH, 660 mg of (2,3-dihydro-1H-indol-3-ylmethyl)dimethylamine are obtained in the form of a yellow solid, the characteristics of which are the following:

Workup

  1. temperaturecooled in an ice bath
  2. extractionalkalinized using 30% sodium hydroxide, and is then extracted with four times 30 ml of ethyl acetate
  3. washThe organic phase is washed with 20 ml of water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customAfter a silica column purification, eluent

Sources & evidence

ORD record
ord-7d4239c7c1bd4c5cb5a96eaa374e3781
Source dataset
uspto-grants-2014_07
Patent number
US08791255B2

Reaction notes

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