Dimethylamine → HCID 67192604, compound

HRID 1841956Notes

Reaction equation

HRID 1841956 reaction equation
[CH:1]([N:4](C(C)C)[CH2:5]C)(C)C.CNC.[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([S:22]([N:25]2[CH2:30][CH2:29][CH:28]([C:31](Cl)=[O:32])[CH2:27][CH2:26]2)(=[O:24])=[O:23])=[CH:18][CH:17]=1)([O-:15])=[O:14]>C(Cl)Cl>[CH3:1][N:4]([CH3:5])[C:31]([CH:28]1[CH2:29][CH2:30][N:25]([S:22]([C:19]2[CH:20]=[CH:21][C:16]([N+:13]([O-:15])=[O:14])=[CH:17][CH:18]=2)(=[O:24])=[O:23])[CH2:26][CH2:27]1)=[O:32]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 86682849HCID 86682849, compound

Product 1

HCID 67192604HCID 67192604, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diisopropylethylamine (0.35 ml, 2.0 mmol) was added in one portion to a stirred solution of dimethylamine (0.8 ml, 1.6 mmol) in DCM (2 ml) at room temperature. To this mixture was added 1-(4-nitro-benzenesulfonyl)-piperidine-4-carbonyl chloride (0.27, 0.8 mmol) in one portion and the mixture was stirred at room temperature under a nitrogen atmosphere for 18 hours. After this time, the mixture was diluted with DCM (20 ml) and washed sequentially by HCl (1M solution, 20 ml) and NaOH (1M solution, 20 ml) before being separated, dried (MgSO4), filtered and concentrated under vacuum to afford the title compound (0.17 g, 33% yield) as an off white solid. Tr=1.65 min m/z (ES+) (M+H+) 342.

Workup

  1. washwashed sequentially by HCl (1M solution, 20 ml) and NaOH (1M solution, 20 ml)
  2. custombefore being separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a645b8ec00db41f1808fdfae4a466c75
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

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