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

HRID 2267923Notes

Reaction equation

HRID 2267923 reaction equation
N1(C[CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([NH:16][C:17]([C:19]3[NH:20][C:21]4[C:26]([CH:27]=3)=[C:25]([O:28][C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=3)[CH:24]=[CH:23][CH:22]=4)=[O:18])[CH2:12][CH2:11]2)CCCCCC1.NC1CCN(C[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)CC1.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>[CH2:9]([N:10]1[CH2:15][CH2:14][CH:13]([NH:16][C:17]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[C:25]([O:28][C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)[CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:12][CH2:11]1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4158521-Benzyl-4-piperidylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 596002614-p-Tolyloxy-1H-indole-2-carboxylic acid [1-(2-azepan-1-yl-ethyl)-piperidin-4-yl]-amide

Product 1

HCID 866134894-p-tolyloxy-1H-indole-2-carboxylic acid (1-benzyl-piperidin-4-yl)-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-p-tolyloxy-1H-indole-2-carboxylic acid (137) (850 mg, 3.2 mmol) and 4-amino-N-benzylpiperidine (605 mg, 3.2 mmol) are dissolved in 5 ml of DMF and after addition of TBTU (1.2 g, 3.5 mmol) and ethyldiisopropylamine (2.2 ml, 12.8 mmol) the mixture is stirred at room temperature for 2 h. Then the mixture is evaporated at high vacuum. The residue is dissolved in ethyl acetate and washed with saturated NaHCO3-solution and brine. The organic layers are dried over Na2SO4, filtrated and evaporated under reduced pressure.

Workup

  1. customThen the mixture is evaporated at high vacuum
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. washwashed with saturated NaHCO3-solution and brine
  4. dry with materialThe organic layers are dried over Na2SO4
  5. filtrationfiltrated
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-cb6fdaeb13844b1fa4e722071a03280d
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

Loading…