Hydrochloric Acid → HCID 23465245, compound

HRID 443736Notes

Reaction equation

HRID 443736 reaction equation
[OH:1][CH:2]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=1)[C:3]([NH:6][C:7](=O)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)([CH3:5])[CH3:4].O1CCCC1.[ClH:33]>O>[ClH:33].[CH3:18][O:17][C:11]1[CH:10]=[C:9]([CH2:8][CH2:7][NH:6][C:3]([CH:2]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=2)[OH:1])([CH3:5])[CH3:4])[CH:14]=[CH:13][C:12]=1[O:15][CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 12570798HCID 12570798, compound

Product 1

HCID 23465245HCID 23465245, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 45 g. (0.12 mole) of N-(β-hydroxy-3-methoxy-α,α-dimethylphenethyl)-3,4-dimethoxybenzeneacetamide in 500 ml. dry tetrahydrofuran is added 200 ml. 1 M (0.2 mole) of BH3 /THF solution over 30 minutes at 0° C. with stirring. After addition, the reaction is allowed to stir overnight at room temperature. Water is added dropwise with caution until effervescence ceases, then 50 ml. more water is added all at once. Aqueous HCl (10%) is added to pH 1.0. Then the acidic reaction mixture is heated at 65° C. for 1 hour to remove most of the tetrahydrofuran and destroy excess BH3. Next, the mixture is cooled with ice and basicified with NH4OH. The mixture is extracted twice with 1 l. ethyl acetate. The combined organic extracts are dried (Na2SO4) and evaporated to dryness in vacuo. The crude hydrochloride is made by dissolving the residue in 250 ml. ethyl acetate and adding a solution of ethyl acetate saturated with dry HCl to pH 2.0. On standing, 25 g. of crude solid is obtained, which is recrystallized from 300 ml. hot isopropanol to give 18.5 g. (39% yield) of α-(1-{[2-(3,4-dimethoxyphenyl)ethyl]amino}-1-methylethyl)-3-methoxybenzenemethanol hydrochloride as a white crystalline solid of analytical purity; m.p. 185°-186° C.

Workup

  1. additionAfter addition
  2. temperatureThen the acidic reaction mixture is heated at 65° C. for 1 hour
  3. customto remove most of the tetrahydrofuran
  4. customdestroy excess BH3
  5. temperatureNext, the mixture is cooled with ice and basicified with NH4OH
  6. extractionThe mixture is extracted twice with 1 l
  7. dry with materialThe combined organic extracts are dried (Na2SO4)
  8. customevaporated to dryness in vacuo
  9. dissolutionby dissolving the residue in 250 ml
  10. additionethyl acetate and adding a solution of ethyl acetate saturated with dry HCl to pH 2.0
  11. customof crude solid is obtained
  12. customwhich is recrystallized from 300 ml
  13. customhot isopropanol to give 18.5 g

Sources & evidence

ORD record
ord-76ef08b1b5f3421e86866b3748bb9df6
Source dataset
uspto-grants-1981_04
Patent number
US04261890

Reaction notes

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