Isoquinoline, 3,4-dihydro-1-((3,4-bis(1-methylethoxy)phenyl)methyl)-6,7-diethoxy-, hydrochloride → 1-({3,4-Bis[(propan-2-yl)oxy]phenyl}methyl)-6,7-diethoxy-1,2,3,4-tetrahydroisoquinoline--hydrogen chloride (1/1)

HRID 325619ノート

反応式

HRID 325619 の反応式
[ClH:1].[CH2:2]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH2:16][CH3:17])[C:11]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH:26]([CH3:28])[CH3:27])=[C:21]([O:29][CH:30]([CH3:32])[CH3:31])[CH:20]=1)=[N:10][CH2:9][CH2:8]2)[CH3:3].[Na]>CO.C(OCC)C.C(OC(C)C)(C)C>[ClH:1].[CH2:2]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH2:16][CH3:17])[CH:11]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH:26]([CH3:28])[CH3:27])=[C:21]([O:29][CH:30]([CH3:32])[CH3:31])[CH:20]=1)[NH:10][CH2:9][CH2:8]2)[CH3:3]

参加物

6

反応物 2

HCID 3052865Isoquinoline, 3,4-dihydro-1-((3,4-bis(1-methylethoxy)phenyl)methyl)-6,7-diethoxy-, hydrochlorideHCID 5360545Sodium

生成物 1

HCID 30528741-({3,4-Bis[(propan-2-yl)oxy]phenyl}methyl)-6,7-diethoxy-1,2,3,4-tetrahydroisoquinoline--hydrogen chloride (1/1)収率 92.5%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 3283Diethyl Ether溶媒HCID 7914Diisopropyl Ether溶媒

実験手順

21 g (0.0455 mole) of 6,7-diethoxy-1-(3',4'-diisopropoxybenzyl)-3,4-dihydroisoquinoline hydrochloride was dissolved in 300 ml of methanol in a 1 liter 3-necked flask. The solution was cooled in an ice/water bath and 2.1 g (0.0555 moles) of sodium borhydride was added in two portions with agitation. Stirring was continued for half an hour, the solvent removed under reduced pressure and the residue obtained taken up in 500 ml of diethyl ether. The ethereal solution was washed 3 times with 200 ml of water, dried over sodium sulphate and the solvent removed under reduced pressure. The oil obtained was dissolved in 20 ml of isopropyl ether, and allowed to crystallize. The product was filtered and re-dissolved in 200 ml of diethyl ether, then a solution of hydrochloric acid in diethyl ether added to pH 2. The solvent was removed under reduced pressure and the residue obtained triturated, firstly in isopropyl ether and then in diethyl ether. After drying, 19.5 g of the title hydrochloride was obtained. Yield=92.5%, m.p. 168° C.

後処理

  1. temperatureThe solution was cooled in an ice/water bath
  2. waitwas continued for half an hour
  3. customthe solvent removed under reduced pressure
  4. customthe residue obtained
  5. washThe ethereal solution was washed 3 times with 200 ml of water
  6. dry with materialdried over sodium sulphate
  7. customthe solvent removed under reduced pressure
  8. customThe oil obtained
  9. customto crystallize
  10. filtrationThe product was filtered
  11. dissolutionre-dissolved in 200 ml of diethyl ether
  12. additiona solution of hydrochloric acid in diethyl ether added to pH 2
  13. customThe solvent was removed under reduced pressure
  14. customthe residue obtained
  15. customtriturated, firstly in isopropyl ether
  16. customAfter drying

出典と根拠

ORDレコード
ord-4b8a8ccb5d6f4992b4eb5b3b71733f70
出典データセット
uspto-grants-1984_04
特許番号
US04442108

反応ノート

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