Benzoyl chloride → 2-Thioureidomethyl-piperidine-1-carboxylic acid tert butyl ester

HRID 18096

반응식

HRID 18096 반응식
C(Cl)(=O)C1C=CC=CC=1.[S-:10][C:11]#[N:12].[Na+].[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[CH2:27][NH2:28])=[O:20])([CH3:17])([CH3:16])[CH3:15]>CC(C)=O>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[CH2:27][NH:28][C:11]([NH2:12])=[S:10])=[O:20])([CH3:17])([CH3:16])[CH3:15]

참가 물질

5

반응물 3

HCID 7412Benzoyl chlorideHCID 516871Sodium thiocyanateHCID 2756482tert-Butyl 2-(aminomethyl)piperidine-1-carboxylate

생성물 1

HCID 865936762-Thioureidomethyl-piperidine-1-carboxylic acid tert butyl ester수율 76.4%

시약·촉매·용매 1

HCID 180Acetone용매2회

실험 절차

Benzoyl chloride (1.2 ml) was added dropwise to sodium thiocyanate (0.90 g) in acetone (50 ml). When the addition was complete the mixture was refluxed for 15 minutes, cooled to room temperature and (RS) 2-aminomethyl-piperidine-1-carboxylic acid tert butyl ester (2.0 g) in acetone (5 ml) added. The mixture was refluxed for 2 hours, cooled to room temperature and solvent removed at reduced pressure. The residue was column chromatographed (silica gel, 0-10% (9:1 methanol/ammonia) in dichloromethane eluant) to give the title product (1.95 g).

후처리

  1. additionWhen the addition
  2. temperaturewas refluxed for 15 minutes
  3. temperatureThe mixture was refluxed for 2 hours
  4. temperaturecooled to room temperature
  5. customsolvent removed at reduced pressure
  6. customchromatographed (silica gel, 0-10% (9:1 methanol/ammonia) in dichloromethane eluant)

출처 및 근거

ORD 기록
ord-c3b3af8c32ee40b2be92cc34eb3ac06c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741329B2

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