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Potassium Carbonate → 4-(3-Dimethylaminomethylene-thioureidomethyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 914720
ノート
印刷プレビュー

反応式

HRID 914720 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH2:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16]([N:24]=[C:25]=[S:26])(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].CO[CH:35](OC)[N:36](C)[CH3:37]>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:25]([N:24]=[CH:16][N:36]([CH3:37])[CH3:35])=[S:26])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 68284Benzoyl isothiocyanateHCID 78373Dimethylformamide dimethyl acetalHCID 7368171-Boc-4-(aminomethyl)piperidine

生成物 1

HCID 724746654-(3-Dimethylaminomethylene-thioureidomethyl)-piperidine-1-carboxylic acid tert-butyl ester収率 79.2%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 17.7 g (82.6 mmol) 4-aminomethyl-piperidine-1-carboxylic acid tert-butyl ester (commercially available) in 150 ml THF was treated with 11.1 ml (82.6 mmol) benzoyl isothiocyanate and stirred for 1 h at room temperature. After evaporation of the solvents the residue was taken up in 100 ml MeOH and treated with 34.2 g (248 mmol) potassium carbonate in 100 ml water. After stirring the mixture for 16 h at room temperature all volatiles were removed and the residue extracted with ethyl acetate. The combined organic layers were washed with saturated NaHCO3 solution and dried with MgSO4. After evaporation of the volatiles 88.1 ml (661 mmol) N,N-dimethylformamide dimethyl acetal was added and the mixture was heated to 110° C. for 16 h. The precipitate was filtered off, washed with n-hexane and dried to yield 21.5 g (79%) of the title compound as pink amorphous solid.

後処理

  1. customAfter evaporation of the solvents the residue
  2. stirringAfter stirring the mixture for 16 h at room temperature all volatiles
  3. customwere removed
  4. extractionthe residue extracted with ethyl acetate
  5. washThe combined organic layers were washed with saturated NaHCO3 solution
  6. dry with materialdried with MgSO4
  7. additionwas added
  8. temperaturethe mixture was heated to 110° C. for 16 h
  9. filtrationThe precipitate was filtered off
  10. washwashed with n-hexane
  11. customdried

出典と根拠

ORDレコード
ord-019b1077bec14d9b827da135577f82bf
出典データセット
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07265109B2

反応ノート

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