1-Methyl-4-piperidone → HCID 21192601, compound

HRID 1068036Notes

Reaction equation

HRID 1068036 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[CH3:15][N:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[CH3:15][N:16]1[CH2:21][CH2:20][CH:19]([NH:1][C:2]2[CH:14]=[CH:13][C:5]([CH2:6][N:7]3[CH2:12][CH2:11][O:10][CH2:9][CH2:8]3)=[CH:4][CH:3]=2)[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 740491-Methyl-4-piperidoneHCID 7768514-(Morpholinomethyl)anilineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 21192601HCID 21192601, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A flask containing 4-(4-aminobenzyl)morpholine from Preparation No. 22 (0.48 g) is treated with tetrhydrofuran (10 mL) and N-methyl-4-piperidone (0.37 mL) under an argon atmosphere. The solution is treated with acetic acid (0.20 mL) followed by sodium triacetoxyborohydride (0.80 g). After stirring overnight, the mixture is partitioned between diethyl ether and saturated aqueous sodium bicarbonate containing sodium hyroxide. The aqueous is back-extracted with additional portions of dichloromethane. The combined organic layer is washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue is purified by flash column chromatography on silica gel eluting with 2% to 5% methanol saturated with ammonia in dichloromethane to afford 0.52 g of 1-methyl-N-[4-(4-morpholinylmethyl)phenyl]-4-piperidinamine as a tan solid.

Workup

  1. customfrom Preparation No
  2. customthe mixture is partitioned between diethyl ether and saturated aqueous sodium bicarbonate
  3. additioncontaining sodium hyroxide
  4. extractionThe aqueous is back-extracted with additional portions of dichloromethane
  5. washThe combined organic layer is washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by flash column chromatography on silica gel eluting with 2% to 5% methanol saturated with ammonia in dichloromethane

Sources & evidence

ORD record
ord-630a26b40bf8487cb2ba38f86b85fe1f
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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