Chloroacetaldehyde → HCID 117987676, compound

HRID 2206030Notes

Reaction equation

HRID 2206030 reaction equation
[CH:1]1([NH2:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.O=[C:8]([CH2:13][C:14]([OH:16])=[O:15])[CH2:9][C:10]([OH:12])=[O:11].Cl[CH2:18][CH:19]=O.Cl>O>[C:10]([CH2:9][C:8]1[N:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:18]=[CH:19][C:13]=1[C:14]([OH:16])=[O:15])([OH:12])=[O:11]

Participants

6

Reactant 4

HCID 33ChloroacetaldehydeHCID 313Hydrochloric AcidHCID 2906CyclopentylamineHCID 68328Acetonedicarboxylic acid

Product 1

HCID 117987676HCID 117987676, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of cyclopentanamine (175 g) in water (150 mL) was added 3-oxopentanedioic acid (30 g) at 20° C. or lower, 2-chloroacetaldehyde (40% aqueous solution, 43 mL) was added dropwise thereto at 10° C. or lower, and the mixture was stirred at room temperature for 14 hr. 6N Hydrochloric acid (150 mL) was added thereto at 0° C., and the black precipitate was removed by filtration. To the filtrate was added 6N hydrochloric acid (50 mL) at 0° C., and the precipitate was collected by filtration to give the title compound (40 g).

Workup

  1. customat 0° C., and the black precipitate was removed by filtration
  2. additionTo the filtrate was added 6N hydrochloric acid (50 mL) at 0° C.
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-c836d268d7e44283bd641f4e1038c864
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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