Dimethyl Sulfoxide → HCID 9966708, compound

HRID 1168840Notes

Reaction equation

HRID 1168840 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6]C=CC=1.[H-].[Na+].[H][H].[CH2:22]([N:29]1CCC(=O)CC1)[C:23]1C=C[CH:26]=[CH:25][CH:24]=1.C[S:37]([CH3:39])=O>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CCC.O>[CH2:14]([CH:11]1[CH2:10][CH2:9][N:8]([CH2:1][CH2:2][CH2:7][C:6]2[S:37][C:39]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:29]=2)[CH2:13][CH2:12]1)[CH2:15][CH2:16][CH3:17]

Participants

8

Reactant 5

HCID 679Dimethyl Sulfoxide2×HCID 192201-Benzyl-4-piperidoneHCID 24758Sodium hydrideHCID 149666561-Benzyl-4-butylidenepiperidineHCID 178418361HCID 178418361, compound

Product 1

HCID 9966708HCID 9966708, compound

Reagents, catalysts & solvents 2

HCID 159628Butyltriphenylphosphonium bromideCatalystHCID 962WaterSolvent

Procedure

1-Benzyl-4-n-butylidenepiperidine (2). A 500 mL 3-necked flask fitted with a stirrer was charged with sodium hydride (1.61 g, 67 mmol) and DMSO (40 mL). The resulting suspension was heated to 90° C. for 30 minutes, until the evolution of hydrogen ceased. The suspension was cooled on an ice-bath for 20 minutes followed by addition of a slurry of butyltriphenylphosphonium bromide (26.6 g, 67 mmol) in DMSO (70 mL). The red mixture was stirred for 15 min at room temperature. 1-Benzyl-4-piperidone 1 (14.0 g, 74 mmol) was slowly added over 30 min, and the mixture was stirred at room temperature over night. H2O (200 mL) was added to the reaction mixture followed by extraction with heptane (4×100 mL) and ethyl acetate (2×100 mL). The combined organic phases were dried and evaporated to dryness, producing 38.1 g of a yellow oil. The oil was distilled to give 14.9 g (88%) of 2, bp 101-105° C. (0.1 mm Hg). 1H NMR (CDCl3) δ0.90-0.95 (t, 3H), 1.25-1.41 (m, 2H), 1.90-2.20 (m, 2H), 2.18-230 (m, 4H), 2.40-2.45 (m, 4H), 2.50 (s, 2H), 5.17 (t, 1H), 7.20-7.42 (m, 5H).

Workup

  1. customA 500 mL 3-necked flask fitted with a stirrer
  2. temperatureThe suspension was cooled on an ice-bath for 20 minutes
  3. stirringthe mixture was stirred at room temperature over night
  4. extractionfollowed by extraction with heptane (4×100 mL) and ethyl acetate (2×100 mL)
  5. customThe combined organic phases were dried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-027a4ace68eb4bee9daa3fe3855f96f7
Source dataset
uspto-grants-2003_09
Patent number
US06627645B2

Reaction notes

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