Triphenylphosphine → Ethyl (1-acetyl-3-{4-[3-(pyridin-2-ylamino)propoxy]benzyl}piperidin-3-yl)acetate

HRID 1860648Notes

Reaction equation

HRID 1860648 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH2:7][C:6]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N+:23]=3[O-])=[CH:13][CH:12]=2)[CH2:5]1)(=[O:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Fe].C(O)(=O)C>[C:1]([N:4]1[CH2:9][CH2:8][CH2:7][C:6]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[CH:15][CH:16]=2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 178470582HCID 178470582, compound

Product 1

HCID 12018737Ethyl (1-acetyl-3-{4-[3-(pyridin-2-ylamino)propoxy]benzyl}piperidin-3-yl)acetateYield 33.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of the product from STEP 9 (335 mg), iron powder (74 mg, 1.3 mmol), triphenylphosphine (236 mg, 0.9 mmol), and acetic acid (6.3 ml) was heated at reflux for 30 min. The cooled reaction was filtered through a short column of Celite®, and washed with ethyl acetate. The filtrate was concentrated to give 108 mg of an colorless oil. This product mixture was used without further purification. The 1H NMR spectrum of the product was consistent for the proposed structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 min
  3. customThe cooled reaction
  4. filtrationwas filtered through a short column of Celite®
  5. washwashed with ethyl acetate
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-187813aefb964ad59e36d8276081a903
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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