Potassium Carbonate → 2-(4-(4-benzylpiperazin-1-yl)cyclohexyl)-N,N-dimethylacetamide

HRID 243564ノート

反応式

HRID 243564 の反応式
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:15]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH3:28][N:29]([CH3:40])[C:30](=[O:39])[CH2:31][CH:32]1[CH2:37][CH2:36][C:35](=O)[CH2:34][CH2:33]1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.C(O)(=O)C>[CH2:15]([N:22]1[CH2:27][CH2:26][N:25]([CH:35]2[CH2:36][CH2:37][CH:32]([CH2:31][C:30]([N:29]([CH3:28])[CH3:40])=[O:39])[CH2:33][CH2:34]2)[CH2:24][CH2:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 759941-BenzylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 59442836N,N-dimethyl-2-(4-oxocyclohexyl)acetamide

生成物 1

HCID 594427712-(4-(4-benzylpiperazin-1-yl)cyclohexyl)-N,N-dimethylacetamide

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium triacetoxyborohydride (1.5 g) is added to a mixture of 1-benzylpiperazine (714 μl), N,N-dimethyl-2-(4-oxocyclohexyl)acetamide (820 mg) and acetic acid (680 μl) in THF (50 ml). The mixture is stirred over night. An aqueous solution of potassium carbonate (20%) is added and the mixture stirred for 30 min. The organic layer is separated and the aqueous layer is extracted with EtOAc. The combined organic layers are washed with satd. aqueous NH4Cl (2×), dried (Na2SO4) and filtered, and the solvent is removed under reduced pressure. The crude product is purified using reverse phase HPLC (Varian C18 Microsorb) eluting with a gradient of 10-100% acetonitrile in water containing 0.2% trifluoroacetic acid to give 2-(4-(4-benzylpiperazin-1-yl)cyclohexyl)-N,N-dimethylacetamide (800 mg). m/z(+) 344 (M+H+). The 2-(pyrrolidin-1-yl)ethanamine and the tert-butyl 4-oxopiperidine-1-carboxylate used to synthesize 34 were purchased from Aldrich. The tert-butyl 3-oxocyclohexylcarbamate used to synthesize 50 was purchased from AB Chem. The 1-benzyl-1,4-diazepane used to synthesize 52 was purchased from Lancaster.

後処理

  1. stirringthe mixture stirred for 30 min
  2. customThe organic layer is separated
  3. extractionthe aqueous layer is extracted with EtOAc
  4. washThe combined organic layers are washed with satd
  5. dry with materialaqueous NH4Cl (2×), dried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent is removed under reduced pressure
  8. customThe crude product is purified
  9. washeluting with a gradient of 10-100% acetonitrile in water containing 0.2% trifluoroacetic acid

出典と根拠

ORDレコード
ord-21c453e2df354f3fadc80e28485e99bc
出典データセット
uspto-grants-2014_02
特許番号
US08653262B2

反応ノート

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