Hydrochloric Acid → 1-(2H-3-chromenyl)-3-(N-methylpiperazino)-1-propanol hydrochloride

HRID 2051645Notes

Reaction equation

HRID 2051645 reaction equation
[ClH:1].[O:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12](=[O:22])[CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)[CH2:3]1.C[O-].[Na+].[BH4-].[K+].Cl>CO>[ClH:1].[O:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH:12]([OH:22])[CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][N:18]([CH3:21])[CH2:19][CH2:20]2)[CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 4192641Potassium borohydrideHCID 10942334Sodium MethoxideHCID 705972641-(2H-3-chromenyl)-3-(N-methyl-piperazino)-1-propanone hydrochloride

Product 1

HCID 705950431-(2H-3-chromenyl)-3-(N-methylpiperazino)-1-propanol hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The hydrochloride (0.1 mole) obtained in Example 1 is dissolved in methanol (400 ml). Sodium methoxide (0.22 mole) in methanol solution is added thereto. The material is cooled to 0°-5° C. and potassium borohydride (0.4 mole) is added thereto. The material is stirred overnight. It is then evaporated in vacuo without heating, taken up into ether/H2O. The ethereal phase is washed with water, dried and evaporated, to give a pale yellow oil which is converted to the hydrochloride by addition of ethereal hydrochloric acid. M.p.=220° C.

Workup

  1. temperatureThe material is cooled to 0°-5° C.
  2. customIt is then evaporated in vacuo
  3. temperaturewithout heating
  4. washThe ethereal phase is washed with water
  5. customdried
  6. customevaporated
  7. customto give a pale yellow oil which

Sources & evidence

ORD record
ord-74382cc0d6f9423088f0067586cf958f
Source dataset
uspto-grants-1980_01
Patent number
US04181722

Reaction notes

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