Hydrochloric Acid → HCID 14230313、化合物

HRID 35243ノート

反応式

HRID 35243 の反応式
[ClH:1].Cl.[NH2:3][C:4]1[CH:26]=[CH:25][C:7]([CH2:8][CH2:9][N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][C:14]([O:22][CH3:23])=[C:15]([O:20]C)[CH:16]=3)[CH:11]2[CH3:24])=[CH:6][CH:5]=1.Cl.CCOCC>Br.CO.C(O)(C)C>[ClH:1].[ClH:1].[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH2:9][N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][C:14]([O:22][CH3:23])=[C:15]([OH:20])[CH:16]=3)[CH:11]2[CH3:24])=[CH:25][CH:26]=1

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 3033629Veradoline Hydrochloride

生成物 1

HCID 14230313HCID 14230313、化合物

試薬・触媒・溶媒 3

HCID 260Hydrogen Bromide溶媒HCID 887Methanol溶媒HCID 3776Isopropanol溶媒

実験手順

N-(4-Aminophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline dihydrochloride (20.0 g, 0.05 m) was suspended in 49% HBr (50 ml) maintained under nitrogen and heated to 120° for 1.5 hr. The mixture was cooled and then poured into 500 cc of ice/water and the solution basified to pH 11 and extracted with ether (3×250 ml). The aqueous phase was buffered to pH 8 by adding glacial acetic acid and dilute NaOH as needed, then extracted with chloroform (4×300 ml). The chloroform extracts were dried over MgSO4 and evaporated to an oil, 8.5 g. This crude product was purified by HPLC on silica gel eluting with ammonia saturated 5% CH3OH/CHCl3. Pure fractions were combined and evaporated to give a yellow oil, 5.5 g. This was dissolved in methanol (20 ml) and isopropanol (10 ml), acidified with HCl gas and the stirred solution treated with ether (100 ml). The solid precipitate was collected by filtration, washed with 10% isopropanol/ether and vacuum dried to give N-(4-aminophenethyl)-1,2,3,4-tetrahydro-6-hydroxy-7-methoxy-1-methylisoquinoline dihydrochloride as a white solid, m.p. 201°-205°.

後処理

  1. temperaturemaintained under nitrogen
  2. temperatureheated to 120° for 1.5 hr
  3. temperatureThe mixture was cooled
  4. extractionextracted with ether (3×250 ml)
  5. additionby adding glacial acetic acid and dilute NaOH
  6. extractionextracted with chloroform (4×300 ml)
  7. dry with materialThe chloroform extracts were dried over MgSO4
  8. customevaporated to an oil, 8.5 g
  9. customThis crude product was purified by HPLC on silica gel eluting with ammonia saturated 5% CH3OH/CHCl3
  10. customevaporated
  11. customto give a yellow oil, 5.5 g
  12. filtrationThe solid precipitate was collected by filtration
  13. washwashed with 10% isopropanol/ether and vacuum
  14. customdried

出典と根拠

ORDレコード
ord-93f46fadcb384f108a04cef5ef4313e1
出典データセット
uspto-grants-1988_08
特許番号
US04766131

反応ノート

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