1,2-Dichloroethane → 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-(2,3-dihydro-1H-inden-2-yl)piperidine-4-carboxamide

HRID 83673Notes

Reaction equation

HRID 83673 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]([OH:26])=O)[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH2:52][CH:53]1[CH2:61][C:60]2[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=2)[CH2:54]1>C(OCC)(=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]([NH:52][CH:53]3[CH2:61][C:60]4[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=4)[CH2:54]3)=[O:26])[CH2:20][CH2:19]2)=[O:17])=[CH:27][CH:28]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 763102-AminoindaneHCID 81531DiisopropylethylamineHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

Product 1

HCID 665716811-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-(2,3-dihydro-1H-inden-2-yl)piperidine-4-carboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The following was added sequentially to DCM (2 mL): 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (50 mg, 0.126 mmol), DIPEA (0.07 mL, 0.378 mmol), EDC (30 mg, 0.151 mmol), HOBT (24 mg, 0.151 mmol), and 2-aminoindane (0.020 mL, 0.151 mmol). The mixture was stirred for 36 h at rt, at which time the solution diluted with a 1:1 solution of ethyl acetate:diethyl ether and washed with 1M HCl (1×), 10% aq. sodium carbonate (1×) and brine (1×), which resulted in a precipitate that failed to go into either phase. The precipitate was collected and washed with water and diethyl ether to afford the title compound as a white solid. (Yield: 52 mg, 0.102 mmol, 81%) 1H NMR (400 MHz, CDCl3) 7.64, 7.33-7.14, 7.03, 6.64, 5.62, 5.51, 4.76, 4.4, 3.33, 2.84-2.75, 2.21, 1.75

Workup

  1. washdiethyl ether and washed with 1M HCl (1×), 10% aq. sodium carbonate (1×) and brine (1×), which
  2. customresulted in a precipitate that
  3. customThe precipitate was collected
  4. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-dc50ff26a2554c36b25185157ccd69f1
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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