Butylamine → HCID 22647827, compound

HRID 852823Notes

Reaction equation

HRID 852823 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 18 (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 19 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-c0476ea2f28043a1acace7523b0b4070
Source dataset
uspto-grants-2007_08
Patent number
US07253207B2

Reaction notes

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