2-(Dimethylamino)ethanol → HCID 53237583, compound

HRID 529966Notes

Reaction equation

HRID 529966 reaction equation
I[C:2]1[S:10][C:9]2[CH2:8][CH2:7][O:6][CH:5](N(C)C(=O)OC(C)(C)C)[C:4]=2[CH:3]=1.[NH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.[CH3:26][N:27](C)CCO>O>[N:20]1([C:2]2[S:10][C:9]3[CH2:8][CH2:7][O:6][CH:5]([CH2:26][NH2:27])[C:4]=3[CH:3]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 8082PiperidineHCID 67256514HCID 67256514, compound

Product 1

HCID 53237583HCID 53237583, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of tert-butyl (2-iodo-6,7-dihydro-4H-thieno[3,2-c]pyran-4-yl)-methylcarbamate (400 mg, 1.0 mmol, 1 eq), piperidine (2 mL), Cu metal (6.4 mg, 1 mmol, 0.1 eq), and K3PO4.3H2O (539.3 mg, 2.34 mmol, 2.3 eq) in 2-dimethylamino-ethanol (deanol) (5 mL) was stirred at 85° C. in a sealed tube for 28 hr. After cooling to room temperature, the reaction mixture was diluted with water, extracted with ethyl acetate, washed with brine, dried over Na2SO4, concentrated and purified by Al2O3 column chromatography. The Boc protecting group was removed with HCl under standard conditions to give the product (2-(piperidin-1-yl)-6,7-dihydro-4H-thieno[3,2-c]pyran-4-yl)methanamine.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by Al2O3 column chromatography
  7. customThe Boc protecting group was removed with HCl under standard conditions

Sources & evidence

ORD record
ord-cc883f62b849419db40deaeea8974d69
Source dataset
uspto-grants-2016_05
Patent number
US09351954B2

Reaction notes

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