1,3-Propanediamine → HCID 59888430, compound

HRID 1838797Notes

Reaction equation

HRID 1838797 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([CH:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[N:6][CH:5]=1.[NH2:33][CH2:34][CH2:35][CH2:36][NH2:37].[C-]#N.[Na+].O>CO>[NH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:3](=[O:2])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([CH:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[N:6][CH:5]=1

Participants

6

Reactant 4

HCID 4281,3-PropanediamineHCID 962WaterHCID 8929Sodium CyanideHCID 59888431HCID 59888431, compound

Product 1

HCID 59888430HCID 59888430, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 15 (473 mg, 1.11 mmol), 1,3-diaminopropane (1.1 ml, 13.1 mmol) and NaCN (7 mg, 0.14 mmol) in methanol (15 ml) was heated under reflux for 24 hours under an Argon atmosphere. After cooling to room temperature the mixture was poured into water (100 ml) and the aqueous layer was washed with ether (2×125 ml), followed by extraction with dichloromethane (3×75 ml). The combined dichloromethane layers were washed with water (50 ml), brine (50 ml) and dried (Na2SO4). Evaporation of the solvent afforded 16 (418 mg, 81%) as a slightly yellow sticky solid. 1H-NMR (CDCl3) δ1.71 (m, 2H), 2.91 (m, 2H), 3.54 (m, 2H), 3.91 (s, 2H), 3.96 (s, 2H), 5.29 (s, 1H), 7.09 (m, 3H), 7.60 (m, 7H), 8.03 (m, 1H), 8.43 (d, 1H, J=4.4 Hz), 8.52 (d, 2H, 4.8 Hz), 8.85 (s, 1H); 1H-NMR (CDCl3) δ30.41 (t), 39.34 (t), 40.51 (t), 56.79 (t), 57.14 (t), 71.86 (d), 121.81(d), 122.07 (d), 122.35 (d), 122.86 (d), 123.82 (d), 128.36 (s), 135.39 (d), 136.23 (d), 136.29 (d), 147.42 (d), 148.95 (d), 149.18 (d), 159.27 (s), 159.58 (s), 162.58 (s), 165.33(s); MS (CI): m/z 468 (M+1).

Workup

  1. temperatureunder reflux for 24 hours under an Argon atmosphere
  2. washthe aqueous layer was washed with ether (2×125 ml)
  3. extractionfollowed by extraction with dichloromethane (3×75 ml)
  4. washThe combined dichloromethane layers were washed with water (50 ml), brine (50 ml)
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-2e9a79ceff614ef68c701dd375f508db
Source dataset
uspto-grants-2004_01
Patent number
US06677288B2

Reaction notes

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