Triethylamine → HCID 67378105, compound

HRID 1182726Notes

Reaction equation

HRID 1182726 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[CH:21](O)[CH3:22])([OH:14])[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>O1CCCC1.CN(C1C=CC=CN=1)C>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[CH:21]([CH3:22])[O:14]2)[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67364898HCID 67364898, compound

Product 1

HCID 67378105HCID 67378105, compoundYield 104.7%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (RS)-1-benzyl-4-[2-(1-hydroxy-ethyl)-phenyl]-piperidin-4-ol (3 g, 9.6 mmol) in tetrahydrofuran (30 ml) was added triethylamine (2.95 ml, 21.2 mmol), dimethylaminopyridine (120 mg, 0.96 mmol) and methanesulfonylchloride (0.84 ml, 10.6 mmol). The reaction mixture was refluxed for 3 hours, cooled to room temperature, quenched with water (15 ml) and ethylacetate (15 ml). The organic phase was dried over Na2SO4 and concentrated in vacuo to yield 2.95 g (quant.) of (RS)-1′-benzyl-3-methyl-3H-spiro[2-benzofuran-1,4′-piperidine] as an orange oil. MS m/e: 294 (M+H+).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. customquenched with water (15 ml) and ethylacetate (15 ml)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-455597d54262489793b772de07155b3d
Source dataset
uspto-grants-2014_03
Patent number
US08664216B2

Reaction notes

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