Hydrochloric Acid → 4-Amino-1-N-Cbz-piperidine

HRID 451299

反応式

HRID 451299 の反応式
C([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:11][CH2:10]1)(OC(C)(C)C)=O.C1COCC1.Cl.[OH-].[Na+]>ClCCl>[NH2:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:13][CH2:14]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21981786Benzyl 4-((tert-butoxycarbonyl)amino)piperidine-1-carboxylate

生成物 1

HCID 178466404-Amino-1-N-Cbz-piperidine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
32.5 °C

実験手順

4-(N—BOC amino)-CBz piperidine (24.4 kg 73.42 mol), THF (65 kg) and 5 M HCl (23.0 kg, 110.13 mol) were combined and heated to 30-35° C. for ˜2 hours, and then at 55° C. overnight. After cooling the reaction mixture to 10° C., dichloromethane (97 kg) and 10M NaOH (7.97 kg, 145.12 mol) were added, while keeping the temperature at <25° C. The phases were separated and the organic phase was washed with 25 wt % NaCl solution (27.5 kg). The washed organic phase was distilled at atmospheric pressure to a volume of 70 L. Dichloromethane (162 kg) was then added, and the mixture was concentrated by distillation to a volume of 120 L to give the title product as a solution in DCM (17.2 kg. 100%.). 1H NMR (CDCl3) 7.33 (5H, m), 5.14 (2H, s), 4.14 (2H, br s), 2.87 (3H, m), 1.83 (2H, m), 1.66 (3H, m) and 1.28 (2H, m).

後処理

  1. customat 55° C.
  2. customovernight
  3. temperatureAfter cooling the reaction mixture to 10° C.
  4. customat <25° C
  5. customThe phases were separated
  6. washthe organic phase was washed with 25 wt % NaCl solution (27.5 kg)
  7. distillationThe washed organic phase was distilled at atmospheric pressure to a volume of 70 L
  8. additionDichloromethane (162 kg) was then added
  9. concentrationthe mixture was concentrated by distillation to a volume of 120 L

出典と根拠

ORDレコード
ord-bf05f1b982934de486754cfd4c208345
出典データセット
uspto-grants-2013_07
特許番号
US08487093B2

関連ノート

読み込み中…