Methyl Isocyanate → HCID 23504788, compound

HRID 351764Notes

Reaction equation

HRID 351764 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]([N:18]3[C:26]4[C:21](=[CH:22][C:23]([Cl:27])=[CH:24][CH:25]=4)[CH:20]=[CH:19]3)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[CH3:28][N:29]=[C:30]=[O:31]>ClCCl>[Cl:27][C:23]1[CH:22]=[C:21]2[C:26](=[CH:25][CH:24]=1)[N:18]([CH:15]1[CH2:14][CH2:13][N:12]([CH2:11][CH:8]3[C:9]4[C:5](=[CH:4][CH:3]=[C:2]([NH:1][C:30]([NH:29][CH3:28])=[O:31])[CH:10]=4)[CH2:6][CH2:7]3)[CH2:17][CH2:16]1)[CH:19]=[CH:20]2

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 23504815HCID 23504815, compound

Product 1

HCID 23504788HCID 23504788, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[1-(6-aminoindan-1-ylmethyl)piperidin-4-yl]-5-chloro-1H-indole, 10h (0.9 g) in dichloromethane (10 mL) was added methylisocyanate (0.2 mL). The mixture was stirred at room temperature for 16 hours. Dichloromethane was evaporated. Upon addition of ethyl acetate the title compound 19a crystallized. The crystalline product was filtered off and dried overnight at 80° C. in vacuo. Yield 0.6 g. mp: 193-195° C. 1H NMR (DMSO-d6): δ 1.70-1.85 (m, 1H); 1.90-2.35 (m, 7H); 2.35-2.85 (m, 4H); 2.65 (d, 3H); 3.05-3.15 (m, 2H); 3.25 (quin, 1H); 4.35-4.45 (m, 1H); 5.95 (dt, 1H); 6.45 (d, 1H); 7.00-7.20 (m, 3H); 7.50-7.65 (m, 4H); 8.35 (s, 1H).

Workup

  1. customDichloromethane was evaporated
  2. additionUpon addition of ethyl acetate the title compound 19a
  3. customcrystallized
  4. filtrationThe crystalline product was filtered off
  5. customdried overnight at 80° C. in vacuo

Sources & evidence

ORD record
ord-359bda2d11234735a45f1d6da8718cd5
Source dataset
uspto-grants-2004_06
Patent number
US06743808B1

Reaction notes

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