Triethylamine → 6-chloro-N-{1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidyl}-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxamide hydrochloride hemihydrate

HRID 329739

반응식

HRID 329739 반응식
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:4][CH:3]1[O:19][CH3:20].C(N(CC)CC)C.[Cl:28][C:29]1[CH:30]=[C:31]([C:41](Cl)=[O:42])[C:32]2[O:37][CH2:36][C:35](=[O:38])[N:34]([CH3:39])[C:33]=2[CH:40]=1>C(Cl)(Cl)Cl>[OH2:11].[ClH:28].[Cl:28][C:29]1[CH:30]=[C:31]([C:41]([NH:1][CH:2]2[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][O:11][C:12]3[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=3)[CH2:4][CH:3]2[O:19][CH3:20])=[O:42])[C:32]2[O:37][CH2:36][C:35](=[O:38])[N:34]([CH3:39])[C:33]=2[CH:40]=1.[Cl:28][C:29]1[CH:30]=[C:31]([C:41]([NH:1][CH:2]2[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][O:11][C:12]3[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=3)[CH2:4][CH:3]2[O:19][CH3:20])=[O:42])[C:32]2[O:37][CH2:36][C:35](=[O:38])[N:34]([CH3:39])[C:33]=2[CH:40]=1.[ClH:28]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 136778321-(3-(4-Fluorophenoxy)propyl)-3-methoxypiperidin-4-amineHCID 299420066-Chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carbonyl chloride

생성물 1

HCID 1317162386-chloro-N-{1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidyl}-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxamide hydrochloride hemihydrate

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

To a solution of 1.2 g of 4-amino-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidine and 1.2 g of triethylamine in 50 ml of chloroform is added a solution of 2.5 g of 6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid chloride in 10 ml of chloroform under cooling and stirring followed by stirring at room temperature for 4 hours. The resultant solution is washed with water, aqueous sodium hydrogen carbonate and then water, and dried over magnesium sulfate. After the solvent is distilled off under reduced pressure, the residue is purified by chromatography on silica gel using chloroform as an eluent, recrystallized from ethanol and treated with ethanolic hydrochloric acid to give 6-chloro-N-{1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidyl}-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxamide hydrochloride hemihydrate, melting at 230° C. with decomposition.

후처리

  1. temperatureunder cooling
  2. stirringby stirring at room temperature for 4 hours
  3. washThe resultant solution is washed with water, aqueous sodium hydrogen carbonate
  4. dry with materialwater, and dried over magnesium sulfate
  5. distillationAfter the solvent is distilled off under reduced pressure
  6. customthe residue is purified by chromatography on silica gel
  7. customrecrystallized from ethanol
  8. additiontreated with ethanolic hydrochloric acid

출처 및 근거

ORD 기록
ord-b1132a501cf940ff9792e2c2591aa29f
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04892872

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