Water → 1'-Benzyl-3H-spiro[2-benzofuran-1,4'-piperidine]

HRID 1782042Notes

Reaction equation

HRID 1782042 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:21][OH:22])(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.O>C1COCC1.CCOC(C)=O>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[CH2:21][O:22]2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 122896691-Benzyl-4-(2-hydroxymethyl-phenyl)-piperidin-4-ol

Product 1

HCID 122130031'-Benzyl-3H-spiro[2-benzofuran-1,4'-piperidine]Yield 94.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
53 °C

Procedure

Crude 1-benzyl-4-(2-hydroxymethyl-phenyl)-piperidin-4-ol (180 g, 0.605 mol) was dissolved in THF (1000 mL). Triethylamine (176.18 mL, 1.27 mol) was added. A solution of methanesulfonyl chloride (33.03 mL, 0.424 mol) in THF (100 mL) was added slowly which caused an increase of the temperature from ambient to 53° C. The reaction was then refluxed for 4 h. Water (500 mL) and AcOEt (500 mL) were added to the reaction mixture. The organic phase was separated, dried and evaporated to give a brown oil (160 g).The crude product was purified by chromatography on silica gel with heptane/AcOEt 100:0 to 60:40 to give a light yellow solid (120 g, 71%). MS: m/z=280 [M+H]+.

Workup

  1. temperatureThe reaction was then refluxed for 4 h
  2. customThe organic phase was separated
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-c6ed65c4c5784155ae2a68b08100f3ea
Source dataset
uspto-grants-2009_03
Patent number
US07498339B2

Reaction notes

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