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

HRID 1660367

반응식

HRID 1660367 반응식
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]

참가 물질

5

반응물 3

HCID 7618TriethanolamineHCID 10928Ethyl chloroformate2회HCID 128015981-(2-Aminophenyl)-1'-methylspiro[indoline-3,4'-piperidine]dihydrochloride

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

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 chloroformate 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.

후처리

  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

출처 및 근거

ORD 기록
ord-32ed2725ab6a472288674baea068fbd2
출처 데이터셋
uspto-grants-1981_12
특허 번호
US04307235

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