Sodium Cyanide → HCID 18431538, compound

HRID 1278974Notes

Reaction equation

HRID 1278974 reaction equation
Cl.[C:2]1([CH:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][CH2:17][CH2:18]O)[CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(Cl)(=O)=O.C1([CH:37](C2C=CC=CC=2)[N:38]2CCC(CCCCOS(C)(=O)=O)CC2)C=CC=CC=1.[C-]#N.[Na+]>ClCCl.CN(C=O)C.C1OCCOCCOCCOCCOC1>[C:2]1([CH:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][CH2:17][CH2:18][C:37]#[N:38])[CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8929Sodium CyanideHCID 31297Methanesulfonyl chlorideHCID 18425715HCID 18425715, compoundHCID 18425743HCID 18425743, compound

Product 1

HCID 18431538HCID 18431538, compound

Reagents, catalysts & solvents 3

HCID 3633615-Crown-5CatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

24.9 (69.2 mmol) 4-(1-diphenylmethyl-piperidin-4-yl)-butan-1-ol hydrochloride are suspended in 160 ml absolute dichloromethane and cooled to ca. 0° C. under moisture exclusion. At this temperature, 16.0 g (159 mmol) TEA are first added and thereafter a solution of 0.3 g (90.0 mmol) methanesulfonoic acid chloride in a little absolute dichloromethane is added dropwise. The mixture is then subsequently stirred for three hours at RT and then placed in ice water. The organic phase is washed once with 50 ml water, dried over sodium sulfate and the solvent is removed under vacuum. The resulting methanesulfonoic acid-4-(1-diphenylmethyl-piperidin-4-yl)-butyl ester is dissolved in 120 ml DMF without further purification and with 7.7 g (158 mmol) sodium cyanide and two drops 15-crown-5 and stirred for six hours at 65° C. After cooling, the mixture is poured in ice water. The precipitated solid is drawn off and dried at 40° C. in high-vacuum. The solid is processed further without additional purification. Yield: 19.9 g (86%).

Workup

  1. washThe organic phase is washed once with 50 ml water
  2. dry with materialdried over sodium sulfate
  3. customthe solvent is removed under vacuum
  4. stirringstirred for six hours at 65° C
  5. temperatureAfter cooling
  6. customdried at 40° C. in high-vacuum
  7. customThe solid is processed further without additional purification

Sources & evidence

ORD record
ord-5bd4f9fe85f24f27af9ade932e6eb335
Source dataset
uspto-grants-2002_09
Patent number
US06444823B1

Reaction notes

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