1-[(3R)-3-(3,4-Dimethoxyphenoxy)-3-phenylpropyl]-4-(4-nitrophenyl)-1,2,3,6-tetrahydropyridine → 4-{1-[(3R)-3-(3,4-Dimethoxyphenoxy)-3-Phenylpropyl]-4-Piperidinyl}Aniline

HRID 2087196Notes

Reaction equation

HRID 2087196 reaction equation
[H][H].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[O:8][C@@H:9]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:10][CH2:11][N:12]1[CH2:17][CH:16]=[C:15]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=2)[CH2:14][CH2:13]1>[Pd].C(O)C>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[O:8][C@@H:9]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH:15]([C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=2)[CH2:16][CH2:17]1

Participants

5

Reactant 2

HCID 695238791-[(3R)-3-(3,4-Dimethoxyphenoxy)-3-phenylpropyl]-4-(4-nitrophenyl)-1,2,3,6-tetrahydropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 695235024-{1-[(3R)-3-(3,4-Dimethoxyphenoxy)-3-Phenylpropyl]-4-Piperidinyl}Aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 25-mL RB flask, equipped with a hydrogen-filled balloon, was charged with 1-[(3R)-3-(3,4-dimethoxyphenoxy)-3-phenylpropyl]-4-(4-nitrophenyl)-1,2,3,6-tetrahydropyridine (63.0 mg, 0.133 mmol), palladium on carbon (5.0 mol-eq%, 0.00665 mmol, 7.04 mg) and ethanol (2.0 mL) at room temperature. After 1 hr the reaction mixture was filtered through a plug of Celite 545 and concentrated under reduced pressure. The crude product (54.1 mg, 89.4%) was used in next reaction without further purification.

Workup

  1. additionfilled balloon
  2. filtrationAfter 1 hr the reaction mixture was filtered through a plug of Celite 545
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product (54.1 mg, 89.4%) was used in next reaction without further purification

Sources & evidence

ORD record
ord-42e0957d6f1446bab0cb6aec6522ff9a
Source dataset
uspto-grants-2004_04
Patent number
US06727264B1

Reaction notes

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