Piperidine → HCID 14054320, compound

HRID 1382860Notes

Reaction equation

HRID 1382860 reaction equation
[C:1]1([C:7]2[C:12]3[S:13][CH:14]=[CH:15][C:11]=3[CH:10]=[C:9]([C:16]([OH:18])=O)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.C1CCCCC1.C(OCC)(=O)C>C1(C)C=CC=CC=1.S(Cl)(Cl)=O>[C:1]1([C:7]2[C:12]3[S:13][CH:14]=[CH:15][C:11]=3[CH:10]=[C:9]([C:16]([N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[O:18])[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 14054310HCID 14054310, compoundHCID 21867204Cyclohexane ethylacetate2×

Product 1

HCID 14054320HCID 14054320, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

The reaction is carried out as in Example 1, but starting with 7-phenylbenzo[b]thiophene-5-carboxylic acid (2.5 g) in toluene (25 cc) and thionyl chloride (2.2 cc) and then triethylamine (4.15 cc) and piperidine (0.97 cc) in toluene (25 cc). After two successive chromatographies of the residue on silica gel, the first with a cyclohexane:ethyl acetate (80:10:10 by volume) mixture as the eluent and the second with a cyclohexane:ethyl acetate (70:30 by volume) mixture as the eluent, a residue is isolated, which is stirred for 1 hour in 40°-60° petroleum spirit. After filtering and drying, 1-[(7-phenylbenzo[b]thien-5-yl)carbonyl]piperidine (1.55 g), m.p. 112° C., is isolated.

Workup

  1. filtrationAfter filtering
  2. customdrying

Sources & evidence

ORD record
ord-0de56bbb7a01437daf97e348252b755d
Source dataset
uspto-grants-1989_02
Patent number
US04808599

Reaction notes

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