4-Aminobenzoic Acid → HCID 66787714, compound

HRID 2194121Notes

Reaction equation

HRID 2194121 reaction equation
C([O:3][C:4]([C:6]1([CH2:22][CH2:23]OC)[CH2:11][CH2:10][N:9]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])(=[O:14])=[O:13])[CH2:8][CH2:7]1)=O)C.[Cl-].C[Al+]C.[NH2:30][C:31]1[CH:39]=[CH:38][C:34]([C:35]([OH:37])=[O:36])=[CH:33][CH:32]=1>CCCCCCC>[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[S:12]([N:9]1[CH2:10][CH2:11][C:6]2([C:4](=[O:3])[N:30]([C:31]3[CH:39]=[CH:38][C:34]([C:35]([OH:37])=[O:36])=[CH:33][CH:32]=3)[CH2:23][CH2:22]2)[CH2:7][CH2:8]1)(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 16686359Dimethylalumanylium chlorideHCID 667876761-(2-Chloro-benzenesulfonyl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 66787714HCID 66787714, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

This material was prepared in analogy to example 1 step D) from 1-(2-chloro-benzenesulfonyl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester (3 g), dimethylaluminium chloride in heptane (1.0 molar, 34.62 ml) and 4-aminobenzoic acid (1.58 g) to give the desired 4-[8-(2-chloro-benzenesulfonyl)-1-oxo-2,8-diaza-spiro[4.5]dec-2-yl]-benzoic acid (0.522 g) as a white solid. MS (ESI): 449.1 (MH+).

Sources & evidence

ORD record
ord-c70caa6e5c75493b836d6ae7cfed82eb
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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