Diisopropylethylamine → 4-(4-Methoxy-phenyl)-1H-indole-2-carboxylic acid (1-benzyl-piperidin-4-yl)-amide

HRID 1929207Notes

Reaction equation

HRID 1929207 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[C:12]([C:18]([OH:20])=O)[NH:13]3)=[CH:5][CH:4]=1.[CH2:21]([N:28]1[CH2:33][CH2:32][CH:31]([NH2:34])[CH2:30][CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C>CN(C=O)C>[CH2:21]([N:28]1[CH2:33][CH2:32][CH:31]([NH:34][C:18]([C:12]2[NH:13][C:14]3[C:10]([CH:11]=2)=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:17]=[CH:16][CH:15]=3)=[O:20])[CH2:30][CH2:29]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4158521-Benzyl-4-piperidylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66841346HCID 66841346, compound

Product 1

HCID 668418814-(4-Methoxy-phenyl)-1H-indole-2-carboxylic acid (1-benzyl-piperidin-4-yl)-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

128 (4.7 g, 17.6 mmol) and 1-benzyl-piperidin-4-ylamine (3.3 g, 17.6 mmol) are dissolved in DMF (70 ml) and after addition of TBTU (6.4 g, 19.4 mmol) and ethyldiisopropylamine (12 ml, 70.4 mmol) the mixture is stirred at room temperature for 2 h. Then the solvent is evaporated at high vacuum. The residue is dissolved in ethyl acetate washed with saturated aqueous sodium hydrogen carbonate and brine. The organic layers are dried over sodium sulfate and evaporated under reduced pressure. The crude mixture is crystallized from methanol.

Workup

  1. customThen the solvent is evaporated at high vacuum
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. washwashed with saturated aqueous sodium hydrogen carbonate and brine
  4. dry with materialThe organic layers are dried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe crude mixture is crystallized from methanol

Sources & evidence

ORD record
ord-e261eb93bc0149a6ac20a98520e4c8cf
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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