4-(3-methyl-piperidino)-tetrahydro-4H-thiopyran-4-carbonitrile → (+/-)-N-[4-(2-benzothiophenyl)-tetrahydro-4H-thiopyran-4-yl]-3-methyl-piperidine

HRID 1251367Notes

Reaction equation

HRID 1251367 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2([C:14]#N)[CH2:13][CH2:12][S:11][CH2:10][CH2:9]2)[CH2:3]1.[S:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH:18]=C1[Mg]Br>CCOCC>[S:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH:18]=[C:14]1[C:8]1([N:4]2[CH2:5][CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3]2)[CH2:13][CH2:12][S:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 183239454-(3-methyl-piperidino)-tetrahydro-4H-thiopyran-4-carbonitrileHCID 178419611HCID 178419611, compound

Product 1

HCID 15408086(+/-)-N-[4-(2-benzothiophenyl)-tetrahydro-4H-thiopyran-4-yl]-3-methyl-piperidine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

4-(3-methyl-piperidino)-tetrahydro-4H-thiopyran-4-carbonitrile (2 g, 8.9 mmoles) dissolved in 50 ml of anhydrous ether is introduced dropwise into a 2-benzothiophenylmagnesium bromide (44.7 mmoles) solution. Ether is heated under reflux for 20 hours. After the usual treatment, a brown oil is obtained (1.7 g) which is chromatographed on 60 g of alumina eluting with an EP/EA (95/5) mixture. In this way, a white solid is obtained (1.2 g, 40%).

Workup

  1. temperatureunder reflux for 20 hours
  2. customAfter the usual treatment, a brown oil is obtained (1.7 g) which
  3. customis chromatographed on 60 g of alumina eluting with an EP/EA (95/5) mixture
  4. customIn this way, a white solid is obtained (1.2 g, 40%)

Sources & evidence

ORD record
ord-9818a6b9dbea43f88644d99626363d02
Source dataset
uspto-grants-2002_01
Patent number
US06342511B1

Reaction notes

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