Acetic Acid → 4-Amino-3-[(1-benzyl-piperidin-4-yl-amino)-methyl]phenol

HRID 1353601Notes

Reaction equation

HRID 1353601 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-])=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=[O:27])C>[Zn]>[NH2:22][C:17]1[CH:18]=[CH:19][C:20]([OH:27])=[CH:21][C:16]=1[CH2:15][NH:14][CH:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 48487621-benzyl-N-[(2-nitrophenyl)methyl]piperidin-4-amine

Product 1

HCID 588643124-Amino-3-[(1-benzyl-piperidin-4-yl-amino)-methyl]phenolYield 79%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Conditions

Temperature
60 °C

Procedure

(1-Benzyl-piperidin-4-yl)-(2-nitro-benzyl)-amine (0.25 g, 0.7 mmol) and zinc dust (0.2 g, excess) were combined in 75% aqueous acetic acid (8 mL) and stirred at 60° C. for 2 h. After cooling to room temperature, the solvents were removed in vacuo and the resultant crude mixture dissolved in water (10 mL), followed by addition of ammonium hydroxide until pH 3 was attained. The solution was extracted with methylene chloride (3×). The organic layers were pooled together, washed with water (2×), brine (2×), dried over sodium sulfate, filtered, and concentrated to afford 0.18 g (79%) of the desired product.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvents were removed in vacuo
  3. dissolutionthe resultant crude mixture dissolved in water (10 mL)
  4. additionfollowed by addition of ammonium hydroxide until pH 3
  5. extractionThe solution was extracted with methylene chloride (3×)
  6. washwashed with water (2×), brine (2×)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-36d2593855fb48988e1af1f51847c936
Source dataset
uspto-grants-2007_05
Patent number
US07220862B2

Reaction notes

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