Chloroform → HCID 13983528, compound

HRID 1084934Notes

Reaction equation

HRID 1084934 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([OH:13])=O)[CH2:4][CH2:3][CH2:2]1.C(Cl)(Cl)Cl.ClC(OCC)=O.[CH2:24]([N:26]1[CH2:30][CH2:29][CH2:28][CH:27]1[CH2:31][NH2:32])[CH3:25]>C(N(CC)CC)C>[CH2:24]([N:26]1[CH2:30][CH2:29][CH2:28][CH:27]1[CH2:31][NH:32][C:11]([C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[O:1][CH2:2][CH2:3][CH2:4]2)=[O:13])[CH3:25]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 10928Ethyl chloroformateHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 127011383,4-Dihydro-2H-1-benzopyran-8-carboxylic acid

Product 1

HCID 13983528HCID 13983528, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

46 g of chroman-8-carboxylic acid, 188 ml of chloroform and 26 g of triethylamine were introduced into a 1-liter round-bottomed flask. The contents were cooled to 0° C. and 28 g of ethyl chloroformate were then added in small amounts, between 0° and 5° C. The contents were stirred for 30 minutes at 5° C. and 36 g of 1-ethyl-2-aminomethylpyrrolidine were then poured in dropwise, between 5° and 10° C. The contents were then stirred for 1 hour at 10° C. and the temperature was then allowed to rise. The chloroform was distilled off under slight vacuum, the residue was taken up with water and acetic acid was added until a pH of 4 was obtained. The solution obtained was filtered with charcoal and then made alkaline with 20% ammonia until a color change of phenolphthalein was observed.

Workup

  1. stirringThe contents were then stirred for 1 hour at 10° C.
  2. distillationThe chloroform was distilled off under slight vacuum
  3. additionwas added until a pH of 4
  4. customwas obtained
  5. customThe solution obtained
  6. filtrationwas filtered with charcoal

Sources & evidence

ORD record
ord-ac91ded54156427894ced06ae9979fd6
Source dataset
uspto-grants-1991_04
Patent number
US05006570

Reaction notes

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