Dimedone → HCID 58797594, compound

HRID 1593019Notes

Reaction equation

HRID 1593019 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][C:7]2[S:8][CH:9]=[C:10]([CH:12]3[CH2:17][CH2:16][N:15](C(OCC=C)=O)[CH2:14][CH2:13]3)[N:11]=2)=[CH:4][CH:3]=1.CC1(C)CC(=O)CC(=O)C1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[S:8][CH:9]=[C:10]([CH:12]3[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]3)[N:11]=2)=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 31358Dimedone2×HCID 69448752HCID 69448752, compound

Product 1

HCID 58797594HCID 58797594, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of allyl 4-[2-(4-chlorobenzyl)-1,3-thiazol-4-yl]piperidine-1-carboxylate (692 mg) in anhydrous THF (20 ml) was added dimedone (2.06 g) followed by Pd(PPh3)4 (201 mg) and the resulting mixture was stirred at room temperature for 4 hours. A further portion of dimedone (1.03 g) and Pd(PPh3)4 (100 Mg) was added and the mixture was stirred for a further 18 hours. The reaction mixture was partitioned between 1N sodium hydroxide (50 ml) and ethyl acetate (100 ml). The organics were separated, dried and evaporated to dryness. The residue was purified by column chromatography on SCX-2 stationary phase using a gradient of DCM up to 50% 7N NH3 in MeOH in dichloromethane as eluent to give 4-[2-(4-chlorobenzyl)-1,3-thiazol-4-yl]piperidine as a solid. Yield 162 mg). NMR (CDCl3): 1.8 (m, 2H), 2.2 (m, 2H), 2.4 (bs, 1H), 2.8-3.0 (m, 3H), 3.3 (m, 2H), 4.4 (s, 2H), 7.4 (m, 5H).

Workup

  1. stirringthe mixture was stirred for a further 18 hours
  2. customThe reaction mixture was partitioned between 1N sodium hydroxide (50 ml) and ethyl acetate (100 ml)
  3. customThe organics were separated
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was purified by column chromatography on SCX-2 stationary phase

Sources & evidence

ORD record
ord-47224396d29f460785e85542ca9fd4f5
Source dataset
uspto-grants-2007_11
Patent number
US07294636B2

Reaction notes

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