Propylenediamine → HCID 63730869, compound

HRID 1687101Notes

Reaction equation

HRID 1687101 reaction equation
[NH2:1][CH2:2][CH:3]([NH2:5])[CH3:4].[S:6](Cl)([CH3:9])(=[O:8])=[O:7].C(N(CC)CC)C>C(Cl)Cl>[NH2:5][CH:3]([CH3:4])[CH2:2][NH:1][S:6]([CH3:9])(=[O:8])=[O:7]

Participants

5

Reactant 3

HCID 6567PropylenediamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 63730869HCID 63730869, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1,2-Diaminopropane (1.00 g, 13.5 mmol, 1.15 mL, 1.1 eq.) was placed in CH2Cl2 (30 mL) and cooled to 0° C. Mesyl chloride (1.40 g, 12.3 mmol, 0.95 mL, 1.0 eq.) was added over a period of five minutes followed by triethylamine (3.72 g, 36.9 mmol, 5.17 mL, 3.0 eq.). The reaction was stirred for 30 minutes and then concentrated under reduced pressure. Purification by basic alumina chromatography using a gradient of 0-15% MeOH/CH2Cl2 as the eluting solvent to obtain N-(2-amino-propyl)-methanesulfonamide as a clear, colorless oil (504 mg, 27%). 1H-NMR (CDCl3, 400 MHz) δ 3.17-3.03 (m, 2H), 2.98 (s, 3H), 2.88-2.80 (m, 1H), 1.12 (d, 3H, J=6.3 Hz).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customPurification by basic alumina chromatography

Sources & evidence

ORD record
ord-4b047e3f29214451b1b0252be8e3d925
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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