Acridan → 10-(3,4,5,6-Tetrahydro-2-pyridyl)acridan

HRID 839380Notes

Reaction equation

HRID 839380 reaction equation
[CH:1]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C:16]1=O.P(Cl)(Cl)(Cl)=O>>[N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=1[N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13][C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]1=2

Participants

4

Reactant 3

HCID 7106AcridanHCID 126652-PiperidoneHCID 24813Phosphorus oxychloride

Product 1

HCID 7060543410-(3,4,5,6-Tetrahydro-2-pyridyl)acridan

Procedure

Reaction of acridan, 2-piperidone and phosphorus oxychloride according to the procedure of Example 1 provides the free base 10-(3,4,5,6-TETRAHYDRO-2-PYRIDYL)ACRIDAN as a distillable oil, b.p. 145°-150° C. at 0.15 mm Hg. Conversion of the free base to the hydrochloride salt affords 10-(3,4,5,5-TETRAHYDRO-2-PYRIDYL)ACRIDAN HYDROCHLORIDE as the hemihydrate, m.p. 190.5°-192.5° C. (corr.) by trituration with hot benzene in a 19% overall yield.

Sources & evidence

ORD record
ord-012374bff8a94ed2b61ca98d1508dbc6
Source dataset
uspto-grants-1978_06
Patent number
US04094981

Reaction notes

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