Propylenediamine → HCID 63730869, compound

HRID 1040793Notes

Reaction equation

HRID 1040793 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-c96bbe9e941c4a9b95866d4e1513c7ed
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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