Hydrochloric Acid → Asenapine

HRID 253744

반응식

HRID 253744 반응식
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[O:22][C:21]3[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=3[C@@H:19]([CH2:27][NH:28][CH3:29])[C@H:18]([C:30](O)=O)[C:17]=2[CH:33]=1.Cl>C1COCC1>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[O:22][C:21]3[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=3[C@H:19]3[CH2:27][N:28]([CH3:29])[CH2:30][C@@H:18]3[C:17]=2[CH:33]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 54751968Dibenz[b,f]oxepin-10-carboxylic acid, 8-chloro-10,11-dihydro-11-[(methylamino)methyl]-, hydrochloride (1:1), (10R,11R)-rel-

생성물 1

HCID 163091Asenapine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a first reaction vessel containing tetrahydrofuran (2.4 mL) at 0° C. was added aluminum chloride (167 mg, 1.26 mmol). To the resulting suspension was slowly added lithium aluminum hydride (3.77 mmol). To a second reaction vessel containing THF (4 mL) was added trans-8-chloro-10,11-dihydro-11-[(methylamino)methyl]-dibenz[b,f]oxepin-10-carboxylic acid hydrochloride (1).HCl (0.4 g, 1.26 mmol). At −10° C., the contents of the first reaction vessel were added to the second reaction vessel. After 30 minutes the reaction mixture was quenched with water and extracted with toluene. The toluene was dried with magnesium sulfate and evaporated. This provided crude trans-5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]-oxepino[4,5-c]pyrrole (A) in nearly quantitative yield with a purity of 63%; 1H-NMR (400.13 MHz in CDCl3 relative to TMS) δ 2.54 (s, 3H), 3.15 (m, 2H), 3.25 and 3.61 (2×m, 4H), 7.01-7.36 (m, 7H).

후처리

  1. additionAt −10° C., the contents of the first reaction vessel were added to the second reaction vessel
  2. customAfter 30 minutes the reaction mixture was quenched with water
  3. extractionextracted with toluene
  4. dry with materialThe toluene was dried with magnesium sulfate
  5. customevaporated

출처 및 근거

ORD 기록
ord-e373b78e297c4d51b5742137e2455d9c
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872147B2

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