Butylamine → HCID 22647827, compound

HRID 479982Notes

Reaction equation

HRID 479982 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=O)[C:6]2[C:11]([C:12]=1[O:13][CH3:14])=[CH:10][CH:9]=[CH:8][CH:7]=2.[CH2:17]([NH2:21])[CH2:18][CH2:19][CH3:20]>CCO.O=[Pt]=O>[CH2:17]([NH:21][CH2:15][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 2

HCID 8007ButylamineHCID 134955543,4-Dimethoxynaphthalene-1-carbaldehyde

Product 1

HCID 22647827HCID 22647827, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent2×

Procedure

A suspension of PtO2 (40 mg) in EtOH (2 mL) was stirred with H2 at 25 psi for 30 min. Naphthaldehyde 518 (596 mg, 2.8 mmol) was dissolved in EtOH and added into the suspension followed by the addition of butylamine (219 mg, 3 mmol). The reaction mixture was hydrogenated for 6 h at 50 psi. The catalyst was filtered through Celite, washed with acetone and the filtrate was concentrated to dryness to give 519 as an oil (665 mg, 87%). The product was utilized in the following step without further purification. 1H NMR (CDCl3) 8.16 (d, J=7.5 Hz, 1H), 7.99 (d, J=7.6 Hz, 2H), 7.40-7.60 (m, 2H), 7.35 (s, 1H), 4.19 (s, 2H), 4.00 (s, 3H), 3.98 (s, 3H), 2.76 (t, J=7.0 Hz, 2H), 1.64 (bs, 1H), 1.45-1.60 (m, 2H), 1.30-1.45 (m, 2H), 0.93 (t, J=7.2 Hz, 3H).

Workup

  1. additionadded into the suspension
  2. waitThe reaction mixture was hydrogenated for 6 h at 50 psi
  3. filtrationThe catalyst was filtered through Celite
  4. washwashed with acetone
  5. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-8ebc1f76cd02417bb037d49a978f7608
Source dataset
uspto-grants-2003_11
Patent number
US06649587B1

Reaction notes

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