1-Pyrrolidinepropanamine → HCID 10520543, compound

HRID 1815455Notes

Reaction equation

HRID 1815455 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.[NH2:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.[S:19](N)(N)(=[O:21])=[O:20]>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][S:19]([NH:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)(=[O:21])=[O:20])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 316701-PyrrolidinepropanamineHCID 660364-ChlorobenzylamineHCID 82267Sulfamide

Product 1

HCID 10520543HCID 10520543, compoundYield 22%

Procedure

A solution of 4-CHLOROBENZYLAMINE (0.610 ml, 5.00 mmol), 1-(3-aminopropyl)pyrrolidine (0.632 ml, 5.00 mmol) and sulfamide (480 mg, 4.99 mol) was heated at reflux for 2 h. The reaction was allowed to cool and partitioned between ethyl acetate (20 ml) and water (20 ml). The aqueous was discarded and the organic phase washed with water (20 ml) and brine (20 ml). The organic phase was dried over anhydrous sodium sulfate and the filtrate was evaporated at reduced pressure. The residue was purified by flash column chromatography (100:10:1 DCM: methanol) to obtain the title compound as a white solid (365 mg, 22%). 1HNMR 7.35-7.28 (4H, m), 4.18 (2H, s), 3.15 (2H, t, 6), 2.61 (2H, t, 6), 2.51 (4H, br m), 1.82-1.67 (6H, m). Microanalysis found C 49.97 H 6.73 N 12.50 C14H22ClN3O2S-0.26H2O requires C 49.96 H 6.74 N 12.49.

Workup

  1. temperatureat reflux for 2 h
  2. temperatureto cool
  3. custompartitioned between ethyl acetate (20 ml) and water (20 ml)
  4. washthe organic phase washed with water (20 ml) and brine (20 ml)
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. customthe filtrate was evaporated at reduced pressure
  7. customThe residue was purified by flash column chromatography (100:10:1 DCM: methanol)

Sources & evidence

ORD record
ord-b2382b8b9d3b4c549826241c8efa00a2
Source dataset
uspto-grants-2005_04
Patent number
US06878736B1

Reaction notes

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