Triethylamine → HCID 20074921, compound

HRID 703775Notes

Reaction equation

HRID 703775 reaction equation
[N:1]1[N:11]2[C:12]3[C:7]([CH2:8][CH2:9][CH2:10]2)=[CH:6][CH:5]=[CH:4][C:3]=3[C:2]=1[C:13]([OH:15])=O.S(Cl)([Cl:18])=O.[NH2:20][CH:21]1[CH:26]2[CH2:27][CH2:28][N:23]([CH2:24][CH2:25]2)[CH2:22]1.C(N(CC)CC)C>C(Cl)Cl>[ClH:18].[N:23]12[CH2:28][CH2:27][CH:26]([CH2:25][CH2:24]1)[CH:21]([NH:20][C:13]([C:2]1[C:3]3=[C:12]4[C:7](=[CH:6][CH:5]=[CH:4]3)[CH2:8][CH2:9][CH2:10][N:11]4[N:1]=1)=[O:15])[CH2:22]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 1232383-AminoquinuclidineHCID 22285716HCID 22285716, compound

Product 1

HCID 20074921HCID 20074921, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.3 g (1.5 mmol) of 7,8-dihydro-6H-pyrazolo[4,5,1-ij]quinoline-2-carboxylic acid were dissolved in 10 ml of methylene chloride. 1 ml of thionyl chloride was added and the mixture was boiled for 1 hour. The mixture was then evaporated in vacuum. 10 ml of methylene chloride, 1.0 g (7.9 mmol) of 3-aminoquinuclidine and 1.0 g (10 mmol) of triethylamine were added after which the mixture was stirred for 30 minutes. The mixture was then extracted with water. The methylene chloride layer was separated, washed with water, dried and evaporated in vacuum. The residue was chromatographed over silicagel using methylene chloride/methanol/ammonia in the ratio 84:15:1 as an eluent; Yield; 0.15 g (33%); melting-point 146°-147.5° C.

Workup

  1. customThe mixture was then evaporated in vacuum
  2. extractionThe mixture was then extracted with water
  3. customThe methylene chloride layer was separated
  4. washwashed with water
  5. customdried
  6. customevaporated in vacuum
  7. customThe residue was chromatographed
  8. custommelting-point 146°-147.5° C.

Sources & evidence

ORD record
ord-3aea275ceb3c4c3399e96b6c14dd4eae
Source dataset
uspto-grants-1991_01
Patent number
US04985424

Reaction notes

Loading…