Chloroform → HCID 20498928, compound

HRID 2166767Notes

Reaction equation

HRID 2166767 reaction equation
[CH:1]1([CH2:9][NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=O)=[CH:13][CH:12]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(Cl)[Cl:22].C(=O)([O-])[O-].[Na+].[Na+].[C:31](Cl)([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32]>O>[C:31]([N:10]([CH2:9][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1)[C:11]1[CH:12]=[CH:13][C:14]([CH2:17][C:18]([Cl:22])=[O:20])=[CH:15][CH:16]=1)([O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:32]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 20499050HCID 20499050, compound

Product 1

HCID 20498928HCID 20498928, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To 15 g. 4-(cyclooctylmethylamino)phenylacetic acid in 200 ml. warm chloroform is added a solution of 12 g. sodium carbonate in 150 ml. water. To the vigorously stirred solution is added 10 g. carbobenzyloxy chloride. After 2 hours stirring at 40° C., the layers are separated, washed three times with 1 N hydrochloric acid, dried, and evaorated to an oil. The oil is dissolved in 30 ml. Prevaporated to an oil. The oil is dissolved in 300 ml. toluene, treated with 15 ml. thionyl chloride and the solution is refluxed for 5 hours. The solvents are evaporated and the residue is dissolved three times in toluene, evaporating each time ultimately to yield 4-(N-carbobenzyloxycyclooctylmethylamino)phenylacetyl chloride as a viscous, orange oil.

Workup

  1. additionTo the vigorously stirred solution is added 10 g
  2. customthe layers are separated
  3. washwashed three times with 1 N hydrochloric acid
  4. customdried
  5. dissolutionThe oil is dissolved in 30 ml
  6. dissolutionThe oil is dissolved in 300 ml
  7. additiontoluene, treated with 15 ml
  8. temperaturethionyl chloride and the solution is refluxed for 5 hours
  9. customThe solvents are evaporated
  10. dissolutionthe residue is dissolved three times in toluene
  11. customevaporating each time ultimately

Sources & evidence

ORD record
ord-7e33767ff97e4e1f92dbc309ef5b9389
Source dataset
uspto-grants-1983_06
Patent number
US04388459

Reaction notes

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