Benzoic Acid → HCID 69058691, compound

HRID 2103095Notes

Reaction equation

HRID 2103095 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([CH3:14])[C:12]=1[CH3:13])[N:9]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:8][C:7]1([CH2:21][CH2:20][CH2:19]1)[CH2:6]2.[C:22](O)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([CH3:14])[C:12]=1[CH3:13])[N:9]([CH2:15][CH2:16][CH2:17][NH:18][C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:8][C:7]1([CH2:19][CH2:20][CH2:21]1)[CH2:6]2

Participants

6

Reactant 3

HCID 243Benzoic AcidHCID 10868DicyclohexylcarbodiimideHCID 69055179HCID 69055179, compound

Product 1

HCID 69058691HCID 69058691, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(6′-methoxy-7′,8′-dimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinoline]-1′-yl)propan-1-amine (80 mg) prepared as described herein, dissolved in 2 mL dichloromethane, was added benzoic acid (67.6 g), 1,3-dicyclohexylcarbodiimide (68.4 mg), 4-dimethylaminopyridine (18 mg) at room temperature. After 2 hours, more dichloromethane was added and the mixture was filtered. The filtrate was concentrated onto silica gel and purified through a column (Hexane/EtOAc, 10:6-10:7), to give N-(3-(6′-methoxy-7′,8′-dimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinoline]-1′-yl)propyl)benzamide (95 mg). Demethylation as described herein gave N-(3-(6′-hydroxy-7′,8′-dimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinoline]-1′-yl)propyl)benzamide (62.4 mg, Hexane/EtOAc, 10:12 as a light yellow oil.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationThe filtrate was concentrated onto silica gel
  3. custompurified through a column (Hexane/EtOAc, 10:6-10:7)

Sources & evidence

ORD record
ord-4a4ef0e5453f4e4eb7574aeefd1e90bc
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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