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

HRID 44135ノート

反応式

HRID 44135 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-41e8d41239dc4af2bcd41db91c2ec37a
出典データセット
uspto-grants-2013_09
特許番号
US08541343B2

反応ノート

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