4-Nitrobenzoyl chloride → HCID 12799174, compound

HRID 851154Notes

Reaction equation

HRID 851154 reaction equation
Cl.Cl.[NH2:3][CH:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:27]=[CH:26][C:17]3[C:18]4[CH2:25][CH2:24][CH2:23][C:19]=4[C:20](=[O:22])[O:21][C:16]=3[CH:15]=2)[CH2:6][CH2:5]1.C(=O)(O)[O-].[Na+].[N+:33]([C:36]1[CH:44]=[CH:43][C:39]([C:40](Cl)=[O:41])=[CH:38][CH:37]=1)([O-:35])=[O:34]>ClCCl>[N+:33]([C:36]1[CH:37]=[CH:38][C:39]([C:40]([NH:3][CH:4]2[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][O:13][C:14]3[CH:27]=[CH:26][C:17]4[C:18]5[CH2:25][CH2:24][CH2:23][C:19]=5[C:20](=[O:22])[O:21][C:16]=4[CH:15]=3)[CH2:6][CH2:5]2)=[O:41])=[CH:43][CH:44]=1)([O-:35])=[O:34]

Participants

5

Reactant 3

HCID 85024-Nitrobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 20502647HCID 20502647, compound

Product 1

HCID 12799174HCID 12799174, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 4.15 g. (0.01 mole) 7-[3-(4-aminopiperidino)-propoxy]-2,3-dihydrocyclopenta[c][1]benzopyran-4(1H)-one dihydrochloride, 2.5 g. sodium bicarbonate and 60 ml. dichloromethane is mixed, while cooling with ice, with a solution of 1.86 g. (0.01 mole) 4-nitrobenzoyl chloride in 20 ml. dichloromethane. The reaction mixture is stirred for 14 hours at ambient temperature, filtered and the precipitate washed with water and dichloromethane and purified by chromatography on silica gel (elution agent dichloromethane:methanol, 9:1 v/v). There are obtained 2.5 g. (51% of theory) of the desired compound; m.p. 212°-213° C.

Workup

  1. additionA mixture of 4.15 g
  2. temperaturewhile cooling with ice, with a solution of 1.86 g
  3. filtrationfiltered
  4. washthe precipitate washed with water and dichloromethane
  5. custompurified by chromatography on silica gel (elution agent dichloromethane:methanol, 9:1 v/v)
  6. customThere are obtained 2.5 g

Sources & evidence

ORD record
ord-cedd2b9ae7bb4217aa1990eafa62e9a5
Source dataset
uspto-grants-1983_05
Patent number
US04382943

Reaction notes

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