Hydrochloric Acid → 1,8-Bis-dimethylamino-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]decane-2,4-dione

HRID 44135노트

반응식

HRID 44135 반응식
C[O:2][C:3]([C:5]1([N:14]([C:18](=[O:29])[CH2:19][C:20]2[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=2[CH3:28])[N:15]([CH3:17])[CH3:16])[CH2:10][CH2:9][N:8]([N:11]([CH3:13])[CH3:12])[CH2:7][CH2:6]1)=O.CC(C)([O-])C.[K+].[OH-].[NH4+].Cl>CN(C)C=O>[CH3:17][N:15]([CH3:16])[N:14]1[C:5]2([CH2:10][CH2:9][N:8]([N:11]([CH3:12])[CH3:13])[CH2:7][CH2:6]2)[C:3](=[O:2])[CH:19]([C:20]2[C:21]([CH3:28])=[CH:22][C:23]([CH3:27])=[CH:24][C:25]=2[CH3:26])[C:18]1=[O:29]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 23665647Potassium tert-butoxideHCID 672274551-Dimethylamino-4-{N',N'-dimethyl-N-[2-(2,4,6-trimethyl-phenyl)-acetyl]-hydrazino}-piperidine-4-carboxylic acid methyl ester

생성물 1

HCID 682286451,8-Bis-dimethylamino-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]decane-2,4-dione수율 32.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Under an atmosphere of argon, a solution of 1.25 g 1-Dimethylamino-4-{N′,N′-dimethyl-N-[2-(2,4,6-trimethyl-phenyl)-acetyl]-hydrazino}-piperidine-4-carboxylic acid methyl ester in 10 ml dry N,N-dimethylformamide is cooled to 5° C., and treated with 1.04 g potassium t-butoxide. The mixture is stirred at ambient temperature for 18 hours, then poured into aqueous ammonium hydroxide, and the pH of the solution adjusted to 4.5 by the addition of aqueous hydrochloric acid. It is extracted three times with ethyl acetate, the organic layer separated, dried over sodium sulfate and evaporated. The residue is purified by chromatography on silica gel with cyclohexane/ethyl acetate (1:3) as a solvent, to yield 377 mg 1,8-Bis-dimethylamino-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]decane-2,4-dione as a solid, mp 80-85° C. 1H-NMR (methanol-d4): 6.91 ppm (s, 2H), 3.18 ppm (m, 2H), 3.08 ppm (m, 2H), 2.93 ppm (s, 6H), 2.48 ppm (s, 6H), 2.35 ppm (m, 2H), 2.29 ppm (s, 3H), 2.14 ppm (s, 6H), 1.40 ppm (m, 2H).

후처리

  1. extractionIt is extracted three times with ethyl acetate
  2. customthe organic layer separated
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue is purified by chromatography on silica gel with cyclohexane/ethyl acetate (1:3) as a solvent

출처 및 근거

ORD 기록
ord-41e8d41239dc4af2bcd41db91c2ec37a
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541343B2

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