Triethylamine → HCID 20074921, compound

HRID 1709728Notes

Reaction equation

HRID 1709728 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 silica gel 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. 13C NMR (CDCl3, ref.: TMS)

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 over silica gel

Sources & evidence

ORD record
ord-e211cb276ccd41d2ad5b4f16a3c6212e
Source dataset
uspto-grants-1990_08
Patent number
US04950759

Reaction notes

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