6-Chloro-1,2,3,4-tetrahydro-4-oxo-1-naphthoyl chloride → 4-(6-Chloro-1,2,3,4-tetrahydro-4-oxo-1-naphthoyl)-3-(pyrrolidin-1-ylmethyl)thiomorpholine hydrochloride

HRID 326750Notes

Reaction equation

HRID 326750 reaction equation
[N:1]1([CH2:6][CH:7]2[CH2:12][S:11][CH2:10][CH2:9][NH:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]([C:24](Cl)=[O:25])[CH2:19][CH2:18][C:17]2=[O:27]>C(N(CC)CC)C>[ClH:13].[Cl:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]([C:24]([N:8]1[CH2:9][CH2:10][S:11][CH2:12][CH:7]1[CH2:6][N:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1)=[O:25])[CH2:19][CH2:18][C:17]2=[O:27]

Participants

4

Reactant 2

HCID 153428706-Chloro-1,2,3,4-tetrahydro-4-oxo-1-naphthoyl chlorideHCID 157301473-(Pyrrolidin-1-ylmethyl)thiomorpholine

Product 1

HCID 189151564-(6-Chloro-1,2,3,4-tetrahydro-4-oxo-1-naphthoyl)-3-(pyrrolidin-1-ylmethyl)thiomorpholine hydrochlorideYield 132.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The procedure described in Example 24 was repeated, but using 1.0 g of 3-(pyrrolidin-1-ylmethyl)thiomorpholine, 1.38 ml of triethylamine and 1.5 g of 6-chloro-1,2,3,4-tetrahydro-4-oxo-1-naphthoyl chloride to afford 1.76 g of the title compound, melting at 195°-200° C.

Sources & evidence

ORD record
ord-63e4432145354b74ac06cfd7400fe49a
Source dataset
uspto-grants-1993_12
Patent number
US05270327

Reaction notes

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