Acetic Acid → HCID 22041386, compound

HRID 1790191Notes

Reaction equation

HRID 1790191 reaction equation
N[C:2]1[CH:11]=[CH:10][C:9]2[C:8]([CH3:13])([CH3:12])[CH2:7][CH2:6][C:5]([CH3:15])([CH3:14])[C:4]=2[CH:3]=1.C=O.[C:18]([BH3-])#[N:19].[Na+].[C:22](O)(=O)C>C(#N)C>[CH3:22][N:19]([CH3:18])[C:2]1[CH:11]=[CH:10][C:9]2[C:8]([CH3:13])([CH3:12])[CH2:7][CH2:6][C:5]([CH3:15])([CH3:14])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 114697605,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine

Product 1

HCID 22041386HCID 22041386, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-amino-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (70.10 g, 0.345 mol) and formaldehyde (280 mL, 10 eq) in 2 L of acetonitrile cooled to 0° C. was added sodium cyanoborohydride (65 g, 3 eq.) in portions while maintaining the temperature between 10–20° C. Glacial acetic acid was added to adjust the pH to 7. The reaction was stirred for 2 hrs at room temperature and the resulting mixture was partitioned between 1N NaOH and EtOAc, the organic phase was washed with water and brine, dried over sodium sulfate, filtered and evaporated. Chromatography on silica gel (hexanes/EtOAc 95:5) gave 54.90 g (70%, 2 steps) of 2-dimethylamino-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene. 1H-NMR (300 MHz, CDCl3): 1.25 (s, 6 H), 1.29 (s, 6 H), 1.66 (s, 4 H), 2.91 (s, 6 H), 6.62 (dd, J=3.0 Hz, J=8.7 Hz, 1 H), 6.67 (d, J=2.7 Hz, 1 H), 7.19 (d, J=8.7 Hz, 1 H).

Workup

  1. temperaturewhile maintaining the temperature between 10–20° C
  2. customthe resulting mixture was partitioned between 1N NaOH and EtOAc
  3. washthe organic phase was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-8c3f080bf557442fbfb92d96788e8437
Source dataset
uspto-grants-2006_07
Patent number
US07071218B2

Reaction notes

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