Hydrochloric Acid → 2-Nitro-4-piperidin-1-ylmethyl-benzoic acid hydrochloride

HRID 512965ノート

反応式

HRID 512965 の反応式
C([O:5][C:6](=[O:24])[C:7]1[CH:12]=[CH:11][C:10]([C:13]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=O)=[CH:9][C:8]=1[N+:21]([O-:23])=[O:22])(C)(C)C.[ClH:25].C([O-])([O-])=O.[K+].[K+]>C1COCC1.C(Cl)Cl.O1CCOCC1>[ClH:25].[N+:21]([C:8]1[CH:9]=[C:10]([CH2:13][N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:11]=[CH:12][C:7]=1[C:6]([OH:24])=[O:5])([O-:23])=[O:22]

参加物

7

反応物 3

HCID 313Hydrochloric Acid2 回HCID 11430Potassium CarbonateHCID 686720862-Nitro-4-(piperidine-1-carbonyl)-benzoic acid tert-butyl ester

生成物 1

HCID 686710012-Nitro-4-piperidin-1-ylmethyl-benzoic acid hydrochloride

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒HCID 312751,4-Dioxane溶媒

実験手順

2-Nitro-4-(piperidine-1-carbonyl)-benzoic acid tert-butyl ester (1.87 mmol) was dissolved in dry THF and added drop-wise to 3.7 mL of borane tetrahydrofuran complex 1.0 M solution, at room temperature, under nitrogen, with stirring. The reaction was then refluxed for six hours, cooled to room temperature and treated carefully with 2N HCl (10 mL) After stirring for 15 minutes, solid K2CO3 was added in portions (1.75 g). The mixture was extracted with EtOAc (3×25 mL). The combined organic layers were dried over sodium sulphate and evaporated leaving an oil that by HPLC-MS analysis resulted a 4:6 mixture of the tertiary amine and the corresponding borane complex. The mixture was dissolved in DCM (1 mL) and treated with 4N HCl in dioxane (7 mL). After 4 days at room temperature, an off white was formed which was filtered, washed with dioxane (5 mL) and dried at 50° C. under vacuum. 0.40 g of title compound were obtained in 70% overall yield.

後処理

  1. additionadded drop-wise to 3.7 mL of borane tetrahydrofuran complex 1.0 M solution
  2. temperatureThe reaction was then refluxed for six hours
  3. temperaturecooled to room temperature
  4. stirringAfter stirring for 15 minutes
  5. extractionThe mixture was extracted with EtOAc (3×25 mL)
  6. dry with materialThe combined organic layers were dried over sodium sulphate
  7. customevaporated
  8. customleaving an oil that by HPLC-MS analysis
  9. customresulted
  10. customan off white was formed which
  11. filtrationwas filtered
  12. washwashed with dioxane (5 mL)
  13. customdried at 50° C. under vacuum

出典と根拠

ORDレコード
ord-21c16b555e4a4239ac2d21ed2beb42d9
出典データセット
uspto-grants-2015_08
特許番号
US09102662B2

反応ノート

読み込み中…