Hexamethylenetetramine → 2-Amino-1-cyclohexylethan-1-one hydrochloride

HRID 1062560Notes

Reaction equation

HRID 1062560 reaction equation
Br[CH2:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].C1N2CN3CN(C2)C[N:12]1C3.C(Cl)(Cl)[Cl:22]>>[ClH:22].[NH2:12][CH2:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6212ChloroformHCID 111600272-Bromo-1-cyclohexylethanone

Product 1

HCID 222816062-Amino-1-cyclohexylethan-1-one hydrochlorideYield 80%

Conditions

Temperature
48 °C

Procedure

According to M6, 2.7 g (13.2 mmol) of 2-bromo-1-cyclohexylethanone (Tetrahedron, 48, 1, 67-78, 1992) are mixed with 1.92 g (13.7 mmol) of hexamethylenetetramine in 20 ml of chloroform. The mixture is heated at 48° C. for 4 hours and then evaporated to dryness. The residue is taken up in 20 ml of ethanol and 9 ml of 36% hydrochloric acid. After leaving overnight at room temperature, the reaction medium is filtered. The filtrate is evaporated to dryness to give an oil which is crystallized from diethyl ether. After filtration and drying, 2.08 g (80%) of 2-amino-1-cyclohexylethanone hydrochloride are obtained in the form of a paste.

Workup

  1. customevaporated to dryness
  2. customAfter leaving overnight at room temperature
  3. filtrationthe reaction medium is filtered
  4. customThe filtrate is evaporated to dryness
  5. customto give an oil which
  6. customis crystallized from diethyl ether
  7. filtrationAfter filtration
  8. customdrying

Sources & evidence

ORD record
ord-162f31b3562f4d37b14b49b48a07245d
Source dataset
uspto-grants-2005_11
Patent number
US06962912B2

Reaction notes

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