1,1'-Carbonyldiimidazole → (+/-)-Decahydro-1-[(3,4-dichlorophenyl)-acetyl]-8-(1-pyrroldinyl)-quinoline

HRID 704855Notes

Reaction equation

HRID 704855 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N1C=CN=C1)(N1C=CN=C1)=O.[N:25]1([CH:30]2[CH:39]3[CH:34]([CH2:35][CH2:36][CH2:37][NH:38]3)[CH2:33][CH2:32][CH2:31]2)[CH2:29][CH2:28][CH2:27][CH2:26]1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:38]2[CH:39]3[CH:34]([CH2:33][CH2:32][CH2:31][CH:30]3[N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[CH2:35][CH2:36][CH2:37]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 798743,4-Dichlorophenylacetic acidHCID 13983380(+/-)-Decahydro-8-(-pyrrolidinyl)-quinoline

Product 1

HCID 13983383(+/-)-Decahydro-1-[(3,4-dichlorophenyl)-acetyl]-8-(1-pyrroldinyl)-quinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 1.98 g of 3,4-dichlorophenyl acetic acid and 1.56 g of carbonyldiimidazole in 17 ml of tetrahydrofuran was stirred at 20° to 22° C. for one hour and the, 1.679 g of [4aRS(4aα, 8α, 8aβ)](±)-decahydro-8-(1-pyrrolidinyl)-quinoline (preparation given at the end of Example (4) were added in solution in 5 ml of tetrahydrofuran. The solution was stirred for 4 hours at 20° to 22° C. and the tetrahydrofuran was eliminated under reduced pressure at less than 45° C. The residue was triturated in 15 ml of ether and in 5 ml of a saturated solution of sodium bicarbonate, then separated and rinsed, first with water then with ether. After drying under reduced pressure, 2.320 g of [4aRS(4aα, 8α, 8aβ)](±)-decahydro-1-[(3,4-dichlorophenyl)-acetyl]-8-(1-pyrrolidinyl)-melting at 138° C. were obtained.

Workup

  1. customwas eliminated under reduced pressure at less than 45° C
  2. customThe residue was triturated in 15 ml of ether and in 5 ml of a saturated solution of sodium bicarbonate
  3. customseparated
  4. washrinsed, first with water
  5. customAfter drying under reduced pressure, 2.320 g of [4aRS(4aα, 8α, 8aβ)](±)-decahydro-1-[(3,4-dichlorophenyl)-acetyl]-8-(1-pyrrolidinyl)-melting at 138° C.
  6. customwere obtained

Sources & evidence

ORD record
ord-298be6756171480f832e2eec6358d904
Source dataset
uspto-grants-1991_01
Patent number
US04988810

Reaction notes

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