Cyanogen Bromide → HCID 86666703, compound

HRID 1470740Notes

Reaction equation

HRID 1470740 reaction equation
[N:1]#[C:2]Br.[NH:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([C@@H:16]([NH:18][C:19](=[O:21])[CH3:20])[CH3:17])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.CCN(C(C)C)C(C)C>C1COCC1.ClCCl>[C:2]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([C@@H:16]([NH:18][C:19](=[O:21])[CH3:20])[CH3:17])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)#[N:1]

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 81531DiisopropylethylamineHCID 67125412(S)-N-[1-(4-piperidin-4-yl-phenyl)ethyl]-acetamide

Product 1

HCID 86666703HCID 86666703, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.37 g (13.0 mmol) Cyanogen bromide are added to a mixture of 2.0 g (8.12 mmol) (S)—N-[1-(4-piperidin-4-yl-phenyl)-ethyl]-acetamide (V.1) and 4.86 mL (28.4 mmol) DIPEA in 15 mL THF and 15 mL dichloromethane. The mixture is stirred for 4 h at rt. After that time, the solvents are removed in vacuo. The residue is taken up in ethylacetate, the mixture is washed with water and the organic layer is concentrated. After addition of diethyl ether the precipitate is collected by filtration, followed by washing with diethylether to yield the desired product.

Workup

  1. customAfter that time, the solvents are removed in vacuo
  2. washthe mixture is washed with water
  3. concentrationthe organic layer is concentrated
  4. additionAfter addition of diethyl ether the precipitate
  5. filtrationis collected by filtration
  6. washby washing with diethylether

Sources & evidence

ORD record
ord-5416f3e277074a5e8a4cbe31e7ff442d
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

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