Water → HCID 70814850, compound

HRID 1852321Notes

Reaction equation

HRID 1852321 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].C(N(CC)CC)C.[F:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1.O>C(Cl)Cl>[F:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8])=[O:22])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 199606-Amino-1-hexanolHCID 678794-Fluorobenzoyl chloride

Product 1

HCID 70814850HCID 70814850, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.0 g (8.53 mmole) of 6-aminohexanol is dissolved in a mixed solution of 17 mL of methylene chloride and 3.6 mL (26 mmol) of triethylamine. After 1 mL (8.53 mmol) of p-fluorobenzoyl chloride is slowly added at 0° C., ice-bath is ended to raise temperature to a room temperature for reaction for 12 hrs. After the reaction, cold water is added to stop the reaction and 20 mL of methylene chloride is used to extract an organic layer to be dried with MgSO4, filtrated and concentrated. Then, re-crystallization is processed in a mixed solution of dichloromethane/n-hexane for obtaining a product of 4-fluoro-N-(6-hydroxyhexyl)-benzamide with a weight of 1.83 g and a yield of 90%. The reactant is confirmed through NMR to be 4-fluoro-N-(6-hydroxyhexyl)-benzamide with a result as follows:

Workup

  1. customice-bath is ended
  2. customfor reaction for 12 hrs
  3. additionis added
  4. extractionto extract an organic layer
  5. dry with materialto be dried with MgSO4
  6. filtrationfiltrated
  7. concentrationconcentrated
  8. customThen, re-crystallization

Sources & evidence

ORD record
ord-33092c26864c4bf6a0909fac91e52224
Source dataset
uspto-grants-2015_02
Patent number
US08961931B2

Reaction notes

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