Phosgene → HCID 20262586, compound

HRID 464796Notes

Reaction equation

C(Cl)(Cl)=O.ClC(OCC)=O.[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2C(=O)O[C:28](=[O:29])[C:27]3=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=[C:26]23)=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[NH:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1>>[CH3:38][O:37][C:34]1[CH:35]=[CH:36][C:26]([NH:25][C:22]2[CH:23]=[CH:24][C:19]([O:18][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:20][CH:21]=2)=[C:27]([CH:33]=1)[C:28]([N:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1)=[O:29]

Participants

Reactant 4

HCID 6371Phosgene

HCID 8082Piperidine

HCID 10928Ethyl chloroformate

HCID 54060996HCID 54060996, compound

Product 1

HCID 20262586HCID 20262586, compound

Procedure

It is contemplated that the foregoing product by reaction with phosgene or ethyl chloroformate can be converted to N-(4-methoxy-2-methylphenyl)isatoic anhydride [VIII; R=H, R"=2-CH3, OR°=4-OCH3 ], and the latter reacted with piperidine to give 1-[2-(4-methoxy-2-methylphenylamino)benzoyl]piperidine [IX; R=H, R"=2-CH3, N=Z=1-piperidinyl, OR°=4-OCH3 ] which can be de-etherified with boron tribromide to yield 1-[2-(4-hydroxy-2-methylphenylamino)benzoyl]piperidine [I; R and R'=H, R"=2-CH3, N=Z=1-piperidinyl, OH at 4-position].

Sources & evidence

ORD record: ord-f4424cf347524035be07fccb1ac7eeae
Source dataset: uspto-grants-1985_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04549016

Reaction notes

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