Triethanolamine → 1-[2-(Ethoxycarbonyl)aminophenyl]-1'-methylspiro[indoline-3,4'-piperidine]

HRID 1632868Notes

Reaction equation

HRID 1632868 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:12]2([CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)[CH2:11]1.N(CCO)(CCO)CCO.Cl[C:36]([O:38][CH2:39][CH3:40])=[O:37]>C(Cl)(Cl)Cl>[CH2:39]([O:38][C:36]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:12]2([CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)[CH2:11]1)=[O:37])[CH3:40]

Participants

5

Reactant 3

HCID 7618TriethanolamineHCID 10928Ethyl chloroformate2×HCID 128015981-(2-Aminophenyl)-1'-methylspiro[indoline-3,4'-piperidine]dihydrochloride

Product 1

HCID 128016081-[2-(Ethoxycarbonyl)aminophenyl]-1'-methylspiro[indoline-3,4'-piperidine]

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A slurry of 10.36 g of 1-(2-aminophenyl)-1'-methylspiro[indoline-3,4'-piperidine] dihydrochloride of Example 1b in 60 ml of chloroform is treated portionwise with 12.3 ml of triethanolamine. The resulting mixture is cooled in an ice bath and treated dropwise over 40 minutes with a solution of 2.7 ml of ethyl chlorformate in 20 ml of chloroform. After stirring at room temperature for 1 hour, an additional 3.0 ml of ethyl chloroformate is added and the mixture is permitted to stand 16 hours. The product is washed thrice with water, brine, dried over anhydrous sodium sulfate, concentrated and pumped on under high vacuum to give a crude carbamate. Chromatography on silica gel (100 g) using ether-methylene chloride affords an oil. The material crystallizes on prolonged standing to yield 1-[2-(ethoxycarbonyl)aminophenyl]-1'-methylspiro[indoline-3,4'-piperidine], mp 99.5°-101.0° C.

Workup

  1. temperatureThe resulting mixture is cooled in an ice bath
  2. waitto stand 16 hours
  3. washThe product is washed thrice with water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto give a crude carbamate
  7. customaffords an oil
  8. customThe material crystallizes on prolonged standing

Sources & evidence

ORD record
ord-6408be419eeb420aaa778909abde3cb1
Source dataset
uspto-grants-1984_10
Patent number
US04477667

Reaction notes

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