Triethylamine → HCID 53643503, compound

HRID 257083Notes

Reaction equation

HRID 257083 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][N:15]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)[CH3:16])=[CH:9][CH:8]=1.C(N(CC)CC)C>O1CCCC1>[C:29]([C:26]1[CH:25]=[CH:24][C:23]([N:20]2[CH2:21][CH2:22][CH:17]([N:15]([CH2:14][CH2:13][C:10]3[CH:9]=[CH:8][C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:12][CH:11]=3)[CH3:16])[CH2:18][CH2:19]2)=[CH:28][CH:27]=1)#[N:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19784344HCID 19784344, compound

Product 1

HCID 53643503HCID 53643503, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.34 g (3 mmol) of methanesulfonyl chloride dissolved in tetrahydrofuran was added dropwise at 0° C. to 1.0 g (3 mmol) of the product from Example 3 and 0.6 g (6 mmol) of triethylamine in 100 ml of anhydrous tetrahydrofuran. The mixture was stirred at room temperature for 16 h and then the solvent was removed under reduced pressure. The residue was partitioned between aqueous sodium bicarbonate solution and methylene chloride, and the organic phase was dried and concentrated under reduced pressure. The resulting oil was purified by chromatography (eluent: methylene chloride/methanol 10:1). 0.73 g of 1-(4-cyanophenyl)-4-(2-(4-methanesulfonylaminophenyl)-N-methylethylamino) piperidine was obtained. 1H NMR (d -DMSO) δ=1.3-1.5 (2H); 1.7 (2H); 2.1 (3H); 2.5-2.7 (4H); 2.7-3.0 (5H); 3.3 (1H); 3.9 (2H); 6.9 (2H); 7.0-7.2 (4H); 7.5 (2H) and 9.6 (1H) ppm.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between aqueous sodium bicarbonate solution and methylene chloride
  3. customthe organic phase was dried
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting oil was purified by chromatography (eluent: methylene chloride/methanol 10:1)

Sources & evidence

ORD record
ord-b18f579367534f5ea533d57d99f262ad
Source dataset
uspto-grants-1993_11
Patent number
US05260318

Reaction notes

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