Methyl Isocyanate → HCID 23504874, compound

HRID 324360Notes

Reaction equation

HRID 324360 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[CH3:25][N:26]=[C:27]=[O:28]>ClCCl>[F:24][C:21]1[CH:20]=[CH:19][C:18]([CH:15]2[CH2:16][CH2:17][N:12]([CH2:11][CH:8]3[C:9]4[C:5](=[CH:4][CH:3]=[C:2]([NH:1][C:27]([NH:26][CH3:25])=[O:28])[CH:10]=4)[CH2:6][CH2:7]3)[CH2:13][CH2:14]2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 235048071-(6-Aminoindan-1-ylmethyl)-4-(4-fluorophenyl)piperidine2×

Product 1

HCID 23504874HCID 23504874, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(6-Aminoindan-1-ylmethyl)-4-(4-fluorophenyl)piperidine, 2a (3 g) was dissolved in dichloromethane (140 ml) and methylisocyanate (0.53 g) was added. The solution was refluxed for 4 hours. Dichloromethane was evaporated and the remaining crude title compound was purified by column chromatography on silica gel (eluted with 4% triethylamine in ethyl acetate). The pure title compound 5a crystallized from diethyl ether. Yield: 0.8 g, mp: 170-173° C. 1H NMR (CDCl3): δ 1.70-1.90 (m, 5 H); 2.00-2.15 (m, 2 H); 2.20-2.35 (m, 1 H); 2.35-2.55 (m, 2 H); 2.60 (dd, 1 H); 2.80 (d, 3 H); 2.75-2.95 (m, 2 H); 3.05 (broad d; 2 H); 3.30 (qui, 1 H); 4.95 (q, 1 H); 6.55 (s, 1 H); 6.90-7.00 (m, 3 H); 7.10-7.25 (m, 3 H); 7.35 (s, 1 H)

Workup

  1. temperatureThe solution was refluxed for 4 hours
  2. customDichloromethane was evaporated
  3. customthe remaining crude title compound was purified by column chromatography on silica gel (eluted with 4% triethylamine in ethyl acetate)
  4. customThe pure title compound 5a crystallized from diethyl ether

Sources & evidence

ORD record
ord-c4438c7d3aa64559afe772c49e30a033
Source dataset
uspto-grants-2001_04
Patent number
US06218394B1

Reaction notes

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