Ethyl 4-isocyanatobenzoate → 1-Methylsufonyl-n-(4-ethoxycarbonylphenyl)spiro[indoline-3,4'-piperidine]-1'-carboxamide

HRID 989053Notes

Reaction equation

HRID 989053 reaction equation
[CH3:1][S:2]([N:5]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:7]2([CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:6]1)(=[O:4])=[O:3].[N:19]([C:22]1[CH:32]=[CH:31][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:24][CH:23]=1)=[C:20]=[O:21]>ClCCl>[CH3:1][S:2]([N:5]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:7]2([CH2:8][CH2:9][N:10]([C:20]([NH:19][C:22]3[CH:23]=[CH:24][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:31][CH:32]=3)=[O:21])[CH2:11][CH2:12]2)[CH2:6]1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 589805Ethyl 4-isocyanatobenzoateHCID 111400731-(Methylsulfonyl)spiro[indoline-3,4'-piperidine]

Product 1

HCID 180048821-Methylsufonyl-n-(4-ethoxycarbonylphenyl)spiro[indoline-3,4'-piperidine]-1'-carboxamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of l-methylsulfonyl-spiro[indoline-3,4′-piperidine] (2.66 g, 10 mmol) in dichloromethane (50 mL), was added ethyl 4-isocyanatobenzoate (1.91 g, 10 mmol) at room temperature. The resulting solution was stirred for four hours during which time precipitation occurred. The mixture was evaporated to remove dichloromethane, and then was suspended in methanol (20 mL), filtration followed by washing with cold methanol gave 1500 as a white solid (4.56 g, 100%)

Workup

  1. customThe mixture was evaporated
  2. customto remove dichloromethane
  3. filtrationfiltration
  4. washby washing with cold methanol

Sources & evidence

ORD record
ord-941a1b40ae4a45f88b83af6b9fc55c58
Source dataset
uspto-grants-2003_10
Patent number
US06638942B1

Reaction notes

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