Methyl Isocyanate → HCID 23504788, compound

HRID 324368Notes

Reaction equation

HRID 324368 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, 1 H); 1.90-2.35 (m, 7 H); 2.35-2.85 (m, 4 H); 2.65 (d, 3 H); 3.05-3.15 (m, 2 H); 3.25 (quin, 1 H); 4.35-4.45 (m, 1 H); 5.95 (dt, 1 H); 6.45 (d, 1 H); 7.00-7.20 (m, 3 H); 7.50-7.65 (m, 4 H); 8.35 (s, 1 H).

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-700800fe6fbf41f5b14a41a7ccda9ed8
Source dataset
uspto-grants-2001_04
Patent number
US06218394B1

Reaction notes

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