Iodine → HCID 66851890, compound

HRID 254628Notes

Reaction equation

HRID 254628 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-76dc9757d17c48a180e137e0db6aac40
Source dataset
uspto-grants-2011_01
Patent number
US07875640B2

Reaction notes

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