Oxalyl chloride → (Oxan-2-yl)(piperazin-1-yl)methanone

HRID 1763455Notes

Reaction equation

[Na+].O1C=CCCC1C([O-])=O.O1CCCCC1C(O)=O.C(Cl)(=O)C(Cl)=O.C(N1CCNCC1)C1C=CC=CC=1.C([N:46]1[CH2:51][CH2:50][N:49]([C:52]([CH:54]2[CH2:59][CH2:58][CH2:57][CH2:56][O:55]2)=[O:53])[CH2:48][CH2:47]1)C1C=CC=CC=1>>[O:55]1[CH2:56][CH2:57][CH2:58][CH2:59][CH:54]1[C:52]([N:49]1[CH2:50][CH2:51][NH:46][CH2:47][CH2:48]1)=[O:53]

Participants

Reactant 5

HCID 65578Oxalyl chloride

HCID 759941-Benzylpiperazine

HCID 10964532Oxane-2-carboxylic acid

HCID 20310402N-benzyl-N'-(tetrahydropyran-2-carbonyl)piperazine

HCID 236651632H-Pyran-2-carboxylic acid, 3,4-dihydro-, sodium salt (1:1)

Product 1

HCID 20385082(Oxan-2-yl)(piperazin-1-yl)methanone

Procedure

To prepare the compound of formula III, the 3,4-dihydro-2H-pyran-2 carboxylic acid sodium salt is hydrogenated to the tetrahydro-pyran-2-carboxylic acid. This compound converted to the acid chloride with oxalyl chloride and is then treated with N-benzyl piperazine. The resultant N-benzyl-N'-(tetrahydropyran-2-carbonyl)piperazine is hydrogenated to give N-(tetrahydro-pyran-2-carbonyl)piperazine. This compound is reacted with the known compound 4-amino-2-chloro-6,7-dimethoxyquinazoline to give the active drug 2-[4-(tetrahydro-pyran-2-carbonyl)piperazinyl]-4-amino-6,7-dimethoxyquinazoline.

Sources & evidence

ORD record: ord-2e957998ccb442fbbe8c965313409e4b
Source dataset: uspto-grants-1978_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04112097

Reaction notes

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