Chloroacetyl chloride → HCID 178520813, compound

HRID 2248033Notes

Reaction equation

HRID 2248033 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([OH:9])[CH2:5][CH2:4]1.[OH-].[Na+].[Cl:12][CH2:13][C:14](Cl)=[O:15]>O>[Cl:12][CH2:13][C:14]([NH:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([OH:9])[CH2:5][CH2:4]1)=[O:15]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 14798Sodium Hydroxide2×HCID 178479278HCID 178479278, compound

Product 1

HCID 178520813HCID 178520813, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

15.1 g. (0.1 mole) trans-4-aminocyclohexanol hydrochloride are suspended in 100 ml. water and adjusted to a pH of 12.5 by the addition of 50 ml. 2N aqueous sodium hydroxide solution. 9.5 ml. (0.12 mole) chloroacetyl chloride are then added dropwise thereto and the pH maintained at 12 to 12.5 by the simultaneous dropwise addition of 2N aqueous sodium hydroxide solution. After the end of the reaction, the reaction mixture is extracted with n-butanol and the organic phase is distilled off in a vacuum. The residue is again dissolved in ethanol, filtered, evaporated and triturated with diethyl ether. After filtering off with suction, there are obtained 12.9 g. of the title compound, i.e. 67% of theory; m.p. 149°-151° C.

Workup

  1. customAfter the end of the reaction
  2. extractionthe reaction mixture is extracted with n-butanol
  3. distillationthe organic phase is distilled off in a vacuum
  4. dissolutionThe residue is again dissolved in ethanol
  5. filtrationfiltered
  6. customevaporated
  7. customtriturated with diethyl ether
  8. filtrationAfter filtering off with suction, there
  9. customare obtained 12.9 g

Sources & evidence

ORD record
ord-897be1d9843743a29e4d6d1693aa8e4c
Source dataset
uspto-grants-1991_08
Patent number
US05037849

Reaction notes

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