2-Aminoheptane → HCID 19107601, compound

HRID 1646527Notes

Reaction equation

HRID 1646527 reaction equation
[NH2:1][CH:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH3:3].C(N(CC)CC)C.[Br:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.[Cl-].[NH4+]>C1COCC1>[CH3:3][CH:2]([NH:1][S:24]([C:21]1[CH:20]=[CH:19][C:18]([CH2:17][Br:16])=[CH:23][CH:22]=1)(=[O:25])=[O:26])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 56032-AminoheptaneHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 27344094-(Bromomethyl)benzenesulfonyl chloride

Product 1

HCID 19107601HCID 19107601, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-aminoheptane (1.67 ml, 0.011 mol) and triethylamine (1.55 ml, 0.011 mol) in dry THF (100 ml) was added powdered 4-bromomethylbenzenesulphonyl chloride (3.0 g, 0.011 mol) in one portion. The mixture was stirred for 3 h at room temperature. The reaction mixture was treated with saturated ammonium chloride (60 ml), extracted with ethyl acetate (3×80 ml), the organics combined and washed with water (50 ml) and brine (50 ml), dried over anhydrous sodium sulphate, filtered and evaporated. The resulting oil was purified by chromatography (silica: 1:2 hexane:ethyl acetate) to give N-1-methylhexyl 4-bromomethylbenzenesulphonamide (1.45 g, 39%) as a pale yellow oil.

Workup

  1. extractionextracted with ethyl acetate (3×80 ml)
  2. washwashed with water (50 ml) and brine (50 ml)
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting oil was purified by chromatography (silica: 1:2 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-66b4cf0c704f4ec4bfb30f0190d96b03
Source dataset
uspto-grants-1993_01
Patent number
US05180723

Reaction notes

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