Methyl Isocyanate → HCID 18960749, compound

HRID 1463310Notes

Reaction equation

HRID 1463310 reaction equation
[CH2:1]([N:3]([CH2:37][CH3:38])[CH2:4][CH:5]([OH:36])[CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:35]=[CH:34][C:14]([C:15]([N:17]2[CH2:22][CH2:21][CH:20]([N:23]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:27][CH2:26][C:24]3=[O:25])[CH2:19][CH2:18]2)=[O:16])=[CH:13][CH:12]=1)[CH3:2].[CH3:39][N:40]=[C:41]=[O:42]>C(#N)C>[CH2:37]([N:3]([CH2:1][CH3:2])[CH2:4][CH:5]([O:36][C:41]([NH:40][CH3:39])=[O:42])[CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([N:17]2[CH2:18][CH2:19][CH:20]([N:23]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:27][CH2:26][C:24]3=[O:25])[CH2:21][CH2:22]2)=[O:16])=[CH:34][CH:35]=1)[CH3:38]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 19031123HCID 19031123, compound

Product 1

HCID 18960749HCID 18960749, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-{1-[4-(6-Diethylamino-5-hydroxyhexyloxy)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (0.7 g) and methyl isocyanate (0.24 ml) are dissolved in acetonitril (20 ml), and thereto is added trifluroboran ethyl ether complex (0.35 ml) under ice-cooling, and the mixture is stirred at room temperature overnight. The reaction mixture is concentrated and purified by silica gel column chromatography (eluent; dichloromethane: methanol=20:1) to give 1-{1-[4-(6-diethylamino-5-methylaminocarbonyloxyhexyloxy)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (314 mg) as colorless oil.

Workup

  1. additionis added trifluroboran ethyl ether complex (0.35 ml) under ice-
  2. temperaturecooling
  3. concentrationThe reaction mixture is concentrated
  4. custompurified by silica gel column chromatography (eluent; dichloromethane: methanol=20:1)

Sources & evidence

ORD record
ord-5ded93264e174294b70a69764b92b07b
Source dataset
uspto-grants-1994_04
Patent number
US05300513

Reaction notes

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