Triethylamine → 4-({[4'-(Methylsulfonyl)-4-biphenylyl]oxy}methyl)-1-piperidinecarbonitrile

HRID 423490Notes

Reaction equation

HRID 423490 reaction equation
[N:1]#[C:2]Br.Cl.[CH3:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)(=[O:8])=[O:7].C(N(CC)CC)C>C(Cl)Cl>[CH3:5][S:6]([C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]3[CH2:28][CH2:27][N:26]([C:2]#[N:1])[CH2:25][CH2:24]3)=[CH:17][CH:16]=2)=[CH:13][CH:14]=1)(=[O:8])=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10476Cyanogen BromideHCID 666725844-({[4'-(Methylsulfonyl)-4-biphenylyl]oxy}methyl)piperidine hydrochloride

Product 1

HCID 866387364-({[4'-(Methylsulfonyl)-4-biphenylyl]oxy}methyl)-1-piperidinecarbonitrileYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyanogen bromide (3.0M in CH2Cl2, 0.1 mL, 0.3 mmol) was added dropwise to a mixture of 4-({[4′-(methylsulfonyl)-4-biphenylyl]oxy}methyl)piperidine hydrochloride (prepared as in Example 2, Step 1, 100 mg, 0.3 mmol) and triethylamine (0.083 mL, 0.6 mmol) in CH2Cl2 (5 mL) at ambient temperature. The reaction mixture was stirred at ambient temperature for 1 h and concentrated. The crude product was purified by chromatography on a silica gel column using 0 to 5% MeOH/CH2Cl2 to give 60 mg (54%) of 4-({[4′-(methylsulfonyl)-4-biphenylyl]oxy}methyl)-1-piperidinecarbonitrile as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.97 (d, 2H, J=8.4 Hz), 7.72 (d, 2H, J=8.6 Hz), 7.55 (d, 2H, J=8.8 Hz), 6.98 (d, 2H, J=8.6 Hz), 3.87 (d, 2H, J=6.2 Hz), 3.58-3.47 (m, 2H), 3.08 (s, 3H), 1.96-1.86 (m, 2H), 1.53 (bs, 5H); LRMS (ESI), m/z 393 (M+Na).

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-29783f355c334326bf275c616fa3487e
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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