Triethylamine → HCID 16658527, compound

HRID 2289823Notes

Reaction equation

HRID 2289823 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:12](Cl)(=[O:14])=[O:13])[CH:10]=2)[C:5]([Cl:16])=[CH:4][N:3]=1.[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C@@H:18]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:12]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][C@@H:18]3[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])(=[O:14])=[O:13])[CH:10]=2)[C:5]([Cl:16])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 166582941,4-Dichloroisoquinoline-7-sulfonyl chlorideHCID 21969834tert-Butyl (R)-2-piperidinecarboxylate

Product 1

HCID 16658527HCID 16658527, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,4-Dichloro-7-isoquinolinylsulphonyl chloride (245 mg, 0.83 mmol) was added to a solution of tert-butyl 2(R)-piperidine carboxylate (153 mg, 0.83 mmol) and triethylamine (170 μl, 1.22 mmol) in CH2Cl2 (15 ml), and the reaction stirred at room temperature for 18 h. The solution was diluted with CH2Cl2, washed with 2M hydrochloric acid, saturated Na2CO3 solution and then brine, dried (MgSO4), and evaporated in vacuo. The residual oil was purified by column chromatography upon silica gel using an elution gradient of pentane-EtOAc (100:0 to 90:10), to give tert-butyl (2R)-1-[(1,4-dichloro-7-isoquinolinyl)sulphonyl]-2-piperidinecarboxylate, (290 mg, 0.65 mmol) as a colourless film.

Workup

  1. washwashed with 2M hydrochloric acid, saturated Na2CO3 solution
  2. dry with materialbrine, dried (MgSO4)
  3. customevaporated in vacuo
  4. customThe residual oil was purified by column chromatography upon silica gel using an elution gradient of pentane-EtOAc (100:0 to 90:10)

Sources & evidence

ORD record
ord-d4f84f249714427d9a75158b0c72eb88
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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