Triethylamine → HCID 88593838, compound

HRID 874520Notes

Reaction equation

HRID 874520 reaction equation
[NH2:1][O:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][O:4]1.C(N(CC)CC)C.[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](Cl)=[O:24]>C(Cl)Cl.CCOC(C)=O>[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:1][O:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][O:4]1)=[O:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 11368152HCID 11368152, compound

Product 1

HCID 88593838HCID 88593838, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

to a solution of H2N-OTHP (1.0 g, 8.54 mmol) and triethylamine (2.46 g, 24.39 mmol) in CH2Cl2 (20 mL) was added a solution of 7-bromoheptanoyl chloride (1.84 g, 8.13 mmol) obtained above in CH2Cl2 (10 mL) dropwise cooling in an ice-water bath. The mixture was stirred at room temperature for 1 h. It was diluted with EtOAc and washed with aqueous saturated NaHCO3, water, and brine, before being dried over MgSO4. Filtration and concentration in vacuo and purification by silica gel flash chromatography (n-hexane/EtOAc=3/1) gave 1.3 g (52%) of 7-bromo-N-(tetrahydro-2H-pyran-2-yloxy)-heptanamide as yellow solid.

Workup

  1. temperaturedropwise cooling in an ice-water bath
  2. washwashed with aqueous saturated NaHCO3, water, and brine
  3. dry with materialbefore being dried over MgSO4
  4. filtrationFiltration and concentration
  5. customin vacuo and purification by silica gel flash chromatography (n-hexane/EtOAc=3/1)

Sources & evidence

ORD record
ord-1680e806ad8943c380150ee295aaf281
Source dataset
uspto-grants-2015_03
Patent number
US08980909B2

Reaction notes

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