Hydrochloric Acid → HCID 53652766, compound

HRID 1761636Notes

Reaction equation

HRID 1761636 reaction equation
Cl.[NH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([O:14][CH3:15])=[C:8]([O:12][CH3:13])[CH:9]=2)[CH:4]1[OH:16].[CH:17](=O)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C([BH3-])#N.[Na+].Cl.C(=O)(O)[O-].[Na+]>CO>[CH3:13][O:12][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][C:7]=1[O:14][CH3:15])[C@@H:4]([OH:16])[C@H:3]([NH:2][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:11]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 454OctanalHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 21242116HCID 21242116, compound

Product 1

HCID 53652766HCID 53652766, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

To a mixture of 2.5 g of 2-amino-5,6-dimethoxy-1-indanol hydrochloride (10.2 mmole) (R. Perrone et al., il Farmaco, Ed. Sci., 39, 255-264, 1984), 1.44 g of octanal (11.2 mmole) and 100 ml of methanol, 2.5 g of sodium cyanoborohydride (39.8 mmole) is added gradually with stirring at 5° C. The mixture is then allowed to stand at room temperature overnight with stirring, then the mixture is made acidic by the addition of dilute HCl while cooling at 5° C., then sodium bicarbonate is added to alkaline reaction and the mixture is extracted with chloroform. The organic phase is dried over sodium sulfate and concentrated under reduced pressure. The crude residue is purified by crystallization from acetone/hexane. Yield 1.5 g (45.7%); m.p. 133°-135° C.

Workup

  1. additionis added gradually
  2. stirringwith stirring
  3. temperaturewhile cooling at 5° C.
  4. extractionthe mixture is extracted with chloroform
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue is purified by crystallization from acetone/hexane

Sources & evidence

ORD record
ord-f6ca4b4b95ce4034aa539f9d730937c6
Source dataset
uspto-grants-1989_05
Patent number
US04826975

Reaction notes

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