Hydrochloric Acid → HCID 13079712, compound

HRID 1731099Notes

Reaction equation

HRID 1731099 reaction equation
CO.[CH2:3]([O:10][C:11]1[CH:41]=[CH:40][C:14]([CH:15]([OH:39])[CH2:16][N:17]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:18]([CH3:31])[CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=2)=[CH:13][C:12]=1[N+:42]([O-])=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.CCCCCC>C1C=CC=CC=1.[Fe]>[NH2:42][C:12]1[CH:13]=[C:14]([CH:40]=[CH:41][C:11]=1[O:10][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH:15]([OH:39])[CH2:16][N:17]([CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[CH:18]([CH3:31])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8058HexaneHCID 13079711HCID 13079711, compound

Product 1

HCID 13079712HCID 13079712, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 241BenzeneSolvent

Procedure

In 50 ml. of methanol there was dissolved 5 g. of 4-benzyloxy-3-nitro-α-[N-benzyl-N-{3-(3,4-dimethoxyphenyl)-1-methylpropyl}aminomethyl]benzyl alcohol and after adding to the solution 2.5 g. of iron powder and 5 ml. of 2N hydrochloric acid, the mixture was refluxed for 50 minutes. After cooling the reaction mixture, the insoluble materials were filtered off, and 5 ml. of a 2N potassium hydride methanol solution and 20 ml. of ethyl acetate were added to the filtrate. The insoluble materials were filtered off and the filtrate was concentrated under a reduced pressure. The residue was extracted with benzene, and the extract was washed with water, dried over anhydrous magnesium sulfate and concentrated under a reduced pressure to provide a yellowish brown viscous product. The product thus obtained was dissolved in benzene and after adding n-hexane until the solution became slightly muddy, the solution was allowed to stand whereby 2.7 g. of yellowish brown crystals of 3-amino-4-benzyloxy-α-[N-benzyl-N-{3-(3,4-dimethoxyphenyl)-1-methylpropyl}aminomethyl] benzyl alcohol [A]were obtained. The product was recrystallized from a mixture of benzene and n-hexane and was characterized by a melting point of 115° C.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. filtrationthe insoluble materials were filtered off
  3. additionof ethyl acetate were added to the filtrate
  4. filtrationThe insoluble materials were filtered off
  5. concentrationthe filtrate was concentrated under a reduced pressure
  6. extractionThe residue was extracted with benzene
  7. washthe extract was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under a reduced pressure
  10. customto provide a yellowish brown viscous product
  11. customThe product thus obtained

Sources & evidence

ORD record
ord-24bbd45edb514d2e9b178d25db5b0a4a
Source dataset
uspto-grants-1976_11
Patent number
US03994974

Reaction notes

Loading…