Hydrochloric Acid → Dibenz[b,f]oxepin-10-carboxylic acid, 8-chloro-10,11-dihydro-11-[(methylamino)methyl]-, hydrochloride (1:1), (10R,11R)-rel-

HRID 2421569ノート

反応式

HRID 2421569 の反応式
Cl.C(OCC)(=[O:4])C.[Cl:8][C:9]1[CH:28]=[CH:27][C:12]2[O:13][C:14]3[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=3[C@H:16]3[CH2:20][N:19]([CH3:21])[C:18](=[O:22])[C@@H:17]3[C:11]=2[CH:10]=1>C1(C)C(C)=CC=CC=1>[ClH:8].[Cl:8][C:9]1[CH:28]=[CH:27][C:12]2[O:13][C:14]3[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=3[C@@H:16]([CH2:20][NH:19][CH3:21])[C@H:17]([C:18]([OH:22])=[O:4])[C:11]=2[CH:10]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 54753299Trans-(+-)-11-chloro-2,3,3a,12b-tetrahydro-2-methyl-1h-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol-1-one

生成物 1

HCID 54751968Dibenz[b,f]oxepin-10-carboxylic acid, 8-chloro-10,11-dihydro-11-[(methylamino)methyl]-, hydrochloride (1:1), (10R,11R)-rel-

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

反応条件

温度
65 °C

実験手順

HCl (55.5 g) and silica gel (55 g) were suspended in xylene (550 mL). The suspension was heated to reflux for 1 night. The reaction mixture was cooled to 65° C. and ethyl acetate (550 mL) was added. The silica gel was filtered off and washed with ethyl acetate (550 mL). The organic phase was evaporated. The crude product was dissolved in methanol (750 mL). The methanol was partly evaporated upon which crystallization of the product takes place. After cooling to 5° C. for 3 hours, the product was obtained by filtration. This yielded trans-11-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol-1-one (IV) (47.8 g, 86%); mp 150.6° C.; 1H-NMR (400.13 MHz in CDCl3 relative to TMS) δ 3.03 (d, 3H), 4.03 (m, 1H), 3.53-3.65 (m, 2H), 3.82 (m, 1H), 7.01-7.28 (m, 6H), 7.87 (dd, 1H).

後処理

  1. temperatureThe suspension was heated
  2. temperatureto reflux for 1 night
  3. filtrationThe silica gel was filtered off
  4. washwashed with ethyl acetate (550 mL)
  5. customThe organic phase was evaporated
  6. dissolutionThe crude product was dissolved in methanol (750 mL)
  7. customThe methanol was partly evaporated upon which crystallization of the product
  8. temperatureAfter cooling to 5° C. for 3 hours
  9. customthe product was obtained by filtration

出典と根拠

ORDレコード
ord-881a96527b21485f861e4b774a81b1f2
出典データセット
uspto-grants-2011_06
特許番号
US07956202B2

反応ノート

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