1-Pyrrolidineethanamine → HCID 3869447, compound

HRID 1815446Notes

Reaction equation

HRID 1815446 reaction equation
[N:1]1([CH2:6][CH2:7][NH2:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1[S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl>[N:1]1([CH2:6][CH2:7][NH:8][S:26]([C:17]2[CH:18]=[CH:19][C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16]=2)(=[O:28])=[O:27])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 13441-PyrrolidineethanamineHCID 71252-Naphthalenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 3869447HCID 3869447, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of 2-pyrrolidin-1-yl-ethylamine (1.00 g, 8.76 mmol) and triethylamine (1.22 ml, 8.76 mmol) in DCM (20 ml) was added portionwise 2-naphthalenesulfonyl chloride (1.98 g, 8.73 mmol). The coolant was removed and the resultant solution was stirred at ambient temperature for 16 h. The organic phase was washed sequentially twice with water (20 ml) and brine (20 ml), and dried over anhydrous magnesium sulfate. The filtrate was evaporated at reduced pressure to obtain the title compound as a white solid (1.81 g, 68%). 1HNMR 8.45 (1H, d, 1.5), 7.99-7.83 (4H, m), 7.66-7.61 (2H, m), 5.80-5.20 (1H, br s), 3.06-3.02 (2H, m), 2.53 (2H, m), 12.36-2.32 (4H, m), 1.74-1.65 (4H, m). Microanalysis found C 62.96 H 6.74; N 9.11. C16H20N2O2S requires C 63.13 H 6.62 N 9:20.

Workup

  1. customThe coolant was removed
  2. washThe organic phase was washed sequentially twice with water (20 ml) and brine (20 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe filtrate was evaporated at reduced pressure

Sources & evidence

ORD record
ord-2698914ef4fc4f35ab234197aeb4c635
Source dataset
uspto-grants-2005_04
Patent number
US06878736B1

Reaction notes

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