Hydrochloric Acid → 3,4,5,6,7,8-Hexahydro-2-(N-phenylphenetylamino)azocine hydrochloride hemihydrate

HRID 1758352

반응식

HRID 1758352 반응식
P(Cl)(Cl)([Cl:3])=[O:2].[C:6]1(=[O:14])[CH2:13]CCCCCN1.[C:15]1([NH:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=CC=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[K+].[N:32]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[ClH:40]>C(O)C.O.ClCCCl>[OH2:2].[ClH:3].[C:22]1([N:21]([C:15]2[CH:16]=[CH:17][C:18]([O:14][CH2:6][CH3:13])=[CH:19][CH:20]=2)[C:33]2[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][N:32]=2)[CH:23]=[CH:24][CH:29]=[CH:28][CH:27]=1.[C:22]1([N:21]([C:33]2[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][N:32]=2)[C:15]2[CH:16]=[CH:17][C:18]([O:14][CH2:6][CH3:13])=[CH:19][CH:20]=2)[CH:23]=[CH:24][CH:29]=[CH:28][CH:27]=1.[ClH:40]

참가 물질

10

반응물 6

HCID 313Hydrochloric Acid2회HCID 12657EnantholactamHCID 14797Potassium HydroxideHCID 24813Phosphorus oxychlorideHCID 74443Benzeneethanamine, N-phenyl-HCID 53438385CID 53438385

생성물 1

HCID 1317129563,4,5,6,7,8-Hexahydro-2-(N-phenylphenetylamino)azocine hydrochloride hemihydrate

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 702Ethanol용매HCID 962Water용매

실험 절차

Phosphorus oxychloride (6.13 g., 0.04 mole) is added in one portion to a stirred mixture of 2-azacyclooctanone (5.1 g., 0.04 mole) and N-phenylphenethylamine (7.9 g., 0.04 mole) in 100 ml. of 1,2-dichloroethane. The mixture is stirred for 16 hr., poured into crushed ice and made basic with 10 N potassium hydroxide. The 1,2-dichloroethane layer is separated, washed with 100 ml. of 1.5 N hydrochloric acid and then with a 100 ml. portion of water. After drying over magnesium sulfate, the 1,2-dichloroethane fraction is concentrated under reduced pressure to provide 10.6 g. of residue which is stirred with water, extracted with ether and then made basic with potassium hydroxide and again extracted with ether. The ethereal extract of the basic mixture is dried (magnesium sulfate) and concentrated under reduced pressure. Distillation of the resulting residue yields 3.5 g., b.p. 152°-170° C./0.15 mm. Hg. of the azocine product free base. The free base is converted to the hydrochloride in ethanol by the addition of ethanolic hydrogen chloride and is recovered by addition of ether affording analytically pure 3,4,5,6,7,8-hexahydro-2-(N-phenylphenethylamino)azocine hydrochloride hemihydrate, m.p. 165°-168° C. (corr.).

후처리

  1. addition, poured
  2. custominto crushed ice
  3. customThe 1,2-dichloroethane layer is separated
  4. washwashed with 100 ml
  5. dry with materialAfter drying over magnesium sulfate
  6. concentrationthe 1,2-dichloroethane fraction is concentrated under reduced pressure
  7. customto provide 10.6 g
  8. extractionextracted with ether
  9. extractionagain extracted with ether
  10. extractionThe ethereal extract of the basic mixture
  11. dry with materialis dried (magnesium sulfate)
  12. concentrationconcentrated under reduced pressure
  13. distillationDistillation of the resulting residue
  14. customyields 3.5 g
  15. customis recovered by addition of ether affording analytically pure 3,4,5,6,7,8-hexahydro-2-(N-phenylphenethylamino)azocine hydrochloride hemihydrate, m.p. 165°-168° C. (corr.)

출처 및 근거

ORD 기록
ord-3409cee5114a40a6ae70bf176325a5d0
출처 데이터셋
uspto-grants-1983_02
특허 번호
US04372887

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