Triethylamine → HCID 13983535, compound

HRID 1084936Notes

Reaction equation

HRID 1084936 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=O)[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.C(N(CC)CC)C.ClC(OCC)=O.[C:27]1([CH2:33][N:34]2[CH2:38][CH2:37][CH2:36][CH:35]2[CH2:39][NH2:40])[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]=1>C(Cl)(Cl)Cl>[C:27]1([CH2:33][N:34]2[CH2:38][CH2:37][CH2:36][CH:35]2[CH2:39][NH:40][C:11]([C:4]2[C:5]3[O:9][CH2:8][CH2:7][C:6]=3[CH:10]=[C:2]([Cl:1])[CH:3]=2)=[O:13])[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 30183171-(1-Cyclohexen-1-ylmethyl)pyrrolidine-2-methylamineHCID 139835345-Chloro-2,3-dihydro-1-benzofuran-7-carboxylic acid

Product 1

HCID 13983535HCID 13983535, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

32 g of 5-chloro-2,3-dihydrobenzofuran-7-carboxylic acid, 130 ml of chloroform and 16 g of triethylamine were introduced into a 1-liter round-bottomed flask. The contents were cooled to 0°-5° C. and 17.5 g of ethyl chloroformate were then added dropwise and the mixture was stirred for 1 hour and 30 minutes. A solution of 34 g of 1-cyclohexenylmethyl-2-aminomethylpyrrolidine in 68 ml of chloroform was then poured in dropwise, between 5° and 10° C., and the mixture was then stirred for 1 hour at 5° C. and for 1 hour at ambient temperature.

Workup

  1. temperatureThe contents were cooled to 0°-5° C.
  2. stirringthe mixture was then stirred for 1 hour at 5° C. and for 1 hour at ambient temperature

Sources & evidence

ORD record
ord-ae3658e172c64bf3ab9df6c1e9b833a8
Source dataset
uspto-grants-1991_04
Patent number
US05006570

Reaction notes

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