Iodine → HCID 66851890, compound

HRID 538769

Reaction equation

HRID 538769 reaction equation
[NH2:1][CH2:2][C:3]1([OH:8])[CH2:7][CH2:6][CH2:5][CH2:4]1.[CH3:9][C:10]([CH3:15])([CH3:14])[CH2:11][CH:12]=O.[S-:16][C:17]#[N:18].[K+].II>C(#N)C>[C:10]([C:11]1[S:16][C:17](=[NH:18])[N:1]([CH2:2][C:3]2([OH:8])[CH2:7][CH2:6][CH2:5][CH2:4]2)[CH:12]=1)([CH3:15])([CH3:14])[CH3:9]

Participants

6

Reactant 4

HCID 807IodineHCID 763353,3-DimethylbutanalHCID 516872Potassium thiocyanateHCID 130512021-(Aminomethyl)cyclopentan-1-ol

Product 1

HCID 66851890HCID 66851890, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(aminomethyl)cyclopentanol (prepared from cyclopentanone as described in WO 2006/100208) (3.5 g, 30 mmol), 3,3-dimethylbutanal (3.4 g, 33 mmol), 4 Å molecular sieves (4 g, 8-12 mesh beads), potassium thiocyanate (3.9 g, 40 mmol) and iodine (7.7 g, 30 mmol) in acetonitrile (50 mL) were processed as described in Example 18A to provide the title compound (5.6 g, 22 mmol, 72% yield). MS (DCI/NH3) m/z 255 (M+H)+.

Sources & evidence

ORD record
ord-a06a0d64612844a88d532f3050cdad5b
Source dataset
uspto-grants-2014_10
Patent number
US08865753B2

Linked notes

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