Acetyl chloride → HCID 19708723, compound

HRID 725784Notes

Reaction equation

HRID 725784 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH:5]1[C:14]2[C:9](=[CH:10][C:11]([S:15]([N:18]3[CH2:24][CH:23]4[CH2:25][CH2:26][CH:20]([CH2:21][CH2:22]4)[CH2:19]3)(=[O:17])=[O:16])=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1.CC(C)([O-])C.[K+]>O1CCCC1>[C:1]([N:5]1[C:14]2[C:9](=[CH:10][C:11]([S:15]([N:18]3[CH2:24][CH:23]4[CH2:25][CH2:26][CH:20]([CH2:21][CH2:22]4)[CH2:19]3)(=[O:17])=[O:16])=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chloride2×HCID 19708701HCID 19708701, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19708723HCID 19708723, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized by addition of acetyl chloride to the compound of Example 41. 3-(1,2,3,4-Tetrahydro-6-quinolinesulfonyl)-3-azabicyclo-[3.2.2]nonane (100 mg, 0.31 mmol) was dissolved in dry tetrahydrofuran. The solution was cooled with an ice bath. Potassium tert-butoxide (76 mg, 0.68 mmol) was added, followed by acetyl chloride (0.03 ml, 0.41 mmol). The mixture was allowed to warm slowly to room temperature as it stirred overnight. The solvent was evaporated and the residue extracted with ethyl acetate. The organics were washed with brine, dried over magnesium sulfate and evaporated to give an orange solid. Purification by chromatotron using chloroform/ethyl acetate (9/1) gave a yellow solid (36 mg, 32% yield): mp 177°-179° C.; 1H NMR (CDCl3): 7.56-7.52 (m, 3 H, aryl H's), 3.80 (t, J=6.3, 2 H, alkyl H's), 3.26 (d, J=4.2, 4 H, N(CH2R)2), 2.82, (t, J=6.6, 2 H, alkyl H's), 2.31 (s, 3 H, CH3), 2.10-1.97 (m, 4 H, N(CH2CHR)2 and alkyl H's), 1.78-1.65 (m, 8 H, alkyl H's).

Workup

  1. temperatureThe solution was cooled with an ice bath
  2. customThe solvent was evaporated
  3. extractionthe residue extracted with ethyl acetate
  4. washThe organics were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customto give an orange solid
  8. customPurification by chromatotron

Sources & evidence

ORD record
ord-e7e1acc2c4e94693983882cd27915b86
Source dataset
uspto-grants-1998_01
Patent number
US05707985

Reaction notes

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