3-Hydroxybenzaldehyde → 1-[(3-Hydroxyphenyl)methyl]piperidin-4-ol

HRID 1981353Notes

Reaction equation

HRID 1981353 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[OH:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[BH4-].[Na+]>CO>[OH:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:5][C:4]2[CH:3]=[C:2]([OH:1])[CH:9]=[CH:8][CH:7]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 79341Piperidin-4-olHCID 4311764Sodium borohydride

Product 1

HCID 133646631-[(3-Hydroxyphenyl)methyl]piperidin-4-olYield 66.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 0.2 mol of 3-hydroxybenzaldehyde in 100 ml of methanol, is added a solution of 0.4 mol of 4-hydroxypiperidine in 80 ml of methanol at about 20° C. To the mixture thus obtained 0.2 mol of sodium borohydride is added portionwise and under stirring, at the temperature of 20°-25° C. within about 90 minutes, then the reaction mixture is stirred 4 hours at room temperature and the solvent is evaporated under reduced pressure to dryness. The residue is taken up with ice and acidified with hydrochloric acid. The acid solution is washed twice with 40 ml of ethyl acetate and concentrated ammonium hydroxide is added thereto up to clearly basic reaction. The product which precipitates is filtered and crystallized from 400 ml of water. The product thus obtained melts at 156°-158° C. Yield: 66.8%.

Workup

  1. stirringthe reaction mixture is stirred 4 hours at room temperature
  2. customthe solvent is evaporated under reduced pressure to dryness
  3. washThe acid solution is washed twice with 40 ml of ethyl acetate and concentrated ammonium hydroxide
  4. additionis added
  5. customup to clearly basic reaction
  6. customThe product which precipitates
  7. filtrationis filtered
  8. customcrystallized from 400 ml of water

Sources & evidence

ORD record
ord-c56fd387ada44b1ea0f925a5bde5c253
Source dataset
uspto-grants-1985_04
Patent number
US04514408

Reaction notes

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