Pentane → (6-Methylsulfanyl-indan-2-yl)-dipropyl-amine

HRID 725921Notes

Reaction equation

HRID 725921 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH:7]([N:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14])[CH2:8]2)=[CH:4][CH:3]=1.[Li]C(C)(C)C.CCCCC.[CH3:28][S:29]SC>C(OCC)C>[CH3:28][S:29][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH:7]([N:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14])[CH2:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8003PentaneHCID 12232Dimethyl DisulfideHCID 21221814(6-Bromo-indan-2-yl)-dipropyl-amineHCID 178418306HCID 178418306, compound

Product 1

HCID 19710198(6-Methylsulfanyl-indan-2-yl)-dipropyl-amineYield 75.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

Distilled (6-bromo-indan-2-yl)-dipropyl-amine (Example 11, 270 mg, 0.91 mmol) was dissolved in dry diethyl ether (20 mL). The solution was kept under argon and cooled to -78° C. A solution of t-BuLi in pentane 1.7M (0.7 mL, 1.20 mmol) was added and the mixture was stired at -78° C. for 1 h. Freshly distilled methyl disulfide (0.14 mL, 1.55 mmol) was added at -78° C. and the mixture was stirred at this temperature for 30 min. The reaction mixture was allowed to reach room temperature and stirred for an additional 1 h. The organic layer was washed with aq. Na2CO3 (5%), the layers separated, dried (Na2CO3) and evaporated to dryness. The crude product was chromatograped (SiO2) using dichloromethane-methanol (45:1) as eluant. The pure fractions were pooled yielding 180 mg (75%) of (6-methylsulfanyl-indan-2-yl)-dipropyl-amine. The free base was converted to the hydrochloride salt and recrystallized from a mixture of 2-propanol and isopropyl ether. m.p. 180-182 (HCl); 1H NMR (300 MHz, CDCl3) δ 0.90 (t, 6H), 1.55 (m, 4H), 2.45-2.60 (m, 7H), 2.80-3.10 (m, 4H), 3.60-3.75. m (1), 7.05-7.20 (m, 3H); 13C NMR (75.4 MHz, CDCl3) δ 12.01, 16.67, 20.21, 36.22, 36.64, 59.43, 63.32, 123.39, 124.81, 125.49, 135.70, 139.38, 142.91; MS m/e 263 (12, M+), 235 (100), 163 (31), 115 (23), 116 (17).

Workup

  1. customto reach room temperature
  2. stirringstirred for an additional 1 h
  3. washThe organic layer was washed with aq. Na2CO3 (5%)
  4. customthe layers separated
  5. dry with materialdried (Na2CO3)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-5d27a24199d84808b34b303b1db41ae6
Source dataset
uspto-grants-1998_01
Patent number
US05708018

Reaction notes

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