Water → HCID 19025805, compound

HRID 1033241Notes

Reaction equation

HRID 1033241 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].C(N(CC)CC)C.[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](Cl)=[O:21].O>O1CCCC1>[OH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:20](=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][Br:15]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 756345-Aminopentan-1-olHCID 5211735-Bromovaleryl chloride

Product 1

HCID 19025805HCID 19025805, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Part A. A solution of 5-aminopentanol (30.0 g, 291 mmol) and triethylamine (50.0 mL, 359 mmol) in tetrahydrofuran (500 mL) was cooled to 0° C., and a solution of 5-bromovaleryl chloride (30.0 mL, 226 mmol) in tetrahydrofuran (200 mL) was added dropwise. After slow warming and stirring for 18 hours, the mixture was poured into water (1 L), and the phases were separated. The aqueous layer was extracted with methylene chloride (2×600 mL). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered and evaporated. The oily product was purified by elution through a silica gel plug with ethyl acetate, and evaporation afforded the product, N-(5-hydroxypentyl)-5-bromopentanamide (47.3 g, 178 mmol, 79%).

Workup

  1. temperatureAfter slow warming
  2. customthe phases were separated
  3. extractionThe aqueous layer was extracted with methylene chloride (2×600 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe oily product was purified by elution through a silica gel plug with ethyl acetate, and evaporation

Sources & evidence

ORD record
ord-5ed814bc21574c87834a634cda006220
Source dataset
uspto-grants-1994_05
Patent number
US05310748

Reaction notes

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