Tert-Butylamine → 3-[4-(4-phenylpiperazino)butyl]indole-5-carboxylic acid N-tert-butylamide

HRID 36954Notes

Reaction equation

HRID 36954 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([C:26]([OH:28])=O)[CH:24]=4)[NH:19][CH:18]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN1CCOCC1.[C:36]([NH2:40])([CH3:39])([CH3:38])[CH3:37].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[C:36]([NH:40][C:26]([C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[C:17]2[CH2:16][CH2:15][CH2:14][CH2:13][N:10]1[CH2:11][CH2:12][N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9]1)=[O:28])([CH3:39])([CH3:38])[CH3:37]

Participants

7

Reactant 5

HCID 6385Tert-ButylamineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 112803583-[4-(4-Phenyl-piperazin-1-yl)-butyl]-1H-indole-5-carboxylic acid

Product 1

HCID 542310883-[4-(4-phenylpiperazino)butyl]indole-5-carboxylic acid N-tert-butylamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 3.74 g of 3-[4-(4-phenylpiperazino)butyl]indole-5-carboxylic acid in 500 ml of DMF is treated with 1.01 g of N-methylmorpholine. A solution of one equivalent of tert-butylamine in 5 ml of DMF, 1.35 g of 1-hydroxybenzotriazole and a solution of 1.92 g of N-(3-dimethylaminopropyl-N'-ethylcarbodiimide hydrochloride in 20 ml of DMF are added with stirring. The mixture is stirred for 16 hours at 20° and the filtrate is evaporated. After working up in a conventional manner, 3-[4-(4-phenylpiperazino)butyl]indole-5-carboxylic acid N-tert-butylamide is obtained.

Workup

  1. stirringThe mixture is stirred for 16 hours at 20°
  2. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-fb01b79ae5084866b09df52fd32128c1
Source dataset
uspto-grants-1995_05
Patent number
US05418237

Reaction notes

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