4-Toluenesulfonyl chloride → HCID 53966560, compound

HRID 725924Notes

Reaction equation

HRID 725924 reaction equation
[CH2:1]([N:4]([CH2:15][CH2:16][CH3:17])[CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:14])[CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].C(N(CC)CC)C.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1.C([O-])([O-])=O.[Na+].[Na+]>ClCCl>[CH2:15]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][S:31]([C:28]3[CH:29]=[CH:30][C:25]([CH3:35])=[CH:26][CH:27]=3)(=[O:33])=[O:32])[CH:11]=2)[CH2:6]1)[CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 127282432-(Dipropylamino)-2,3-dihydro-1H-inden-5-ol

Product 1

HCID 53966560HCID 53966560, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Dipropylamino-indan-5-ol (Preparation 9, 140 mg, 0.47 mmol) was dissolved in dichloromethane (25 mL) and cooled to 0 C. Thereafter was added triethylamine (99 mg, 0.98 mmol) and toluene-4-sulfonyl chloride (101 mg, 0.54 mmol). The reaction mixture was allowed to reach room temperature and was then stirred at ambient temperature for 2 h. Aqueous Na2CO3 solution (25 mL, 10%) was added and the mixture was stirred for an additional 5 min. The layers were separated and the organic layer was washed, dried (Na2SO4) and the solvent evaporated. The crude product was chromatograped using dichloromethane-methanol (19:1) as eluant. The pure fractions were pooled, and the solvent removed in vacuo yielding 135 mg (78%) of toluene-4-sulfonic acid 2-dipropylamino-indan-5-yl ester as an oil. The amine was converted to its hydrochloride salt (hydroscopic).; 1H NMR (300 MHz, CDCl3) δ 0.85 (t, 6H), 1.45 (m, 4H), 2.4-2.5 (m, 7H), 2.75-2.85 (m, 2H), 2.90-3.00 (m, 2H), 3.60-3.70 (m, 1H), 6.65 (dd, J=2.5, 8.3 Hz, 1H), 6.85 (d, J=2.5 Hz, 1H), 7.05 (d, J=8.0 Hz, 1H), 7.30 (d, J=8.5 Hz, 2H), 7.70 (d, J=8.7 Hz, 2H); 13C NMR (75.4 MHz, CDCl3) δ 11.99, 20.24, 21.73, 36.11, 36.70, 53.37, 63.44, 118.57, 120.14, 125.03, 128.51, 129.67, 132.60, 140.96, 143.74, 145.16, 148.27; MS m/e 387 (3, M+), 358 (100), 232 (49), 91 (15), 155 (13).

Workup

  1. temperaturecooled to 0 C
  2. customto reach room temperature
  3. stirringthe mixture was stirred for an additional 5 min
  4. customThe layers were separated
  5. washthe organic layer was washed
  6. dry with materialdried (Na2SO4)
  7. customthe solvent evaporated
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-36cd08cd0df2480eb6c9f993df0dd2c0
Source dataset
uspto-grants-1998_01
Patent number
US05708018

Reaction notes

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