Hydrochloric Acid → HCID 86753654, compound

HRID 361707Notes

Reaction equation

HRID 361707 reaction equation
[ClH:1].[CH2:2]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][NH:17][CH:18]([CH3:20])[CH3:19])[CH:8]=[O:9])[CH:3]=[CH2:4]>C(O)C>[ClH:1].[CH2:2]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][NH:17][CH:18]([CH3:20])[CH3:19])[CH:8]=[O:9])[CH:3]=[CH2:4]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 54074145HCID 54074145, compound

Product 1

HCID 86753654HCID 86753654, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1M aqueous hydrochloric acid (2 ml) was added to 3-allyl-4-(3-[N-isopropylamino]propoxy)benzaldehyde, 2-(1,3-dioxane)acetal (200 mg) and stirred for 16 hours at ambient temperature. The reaction mixture was evaporated and the residue purified by flash column chromatography on silica gel (Merck Art No 9385) using a 90:8:2 (v/v/v) mixture of ethyl acetate/methanol/ammonia (density=0.88 g/cm 3) as eluent. The crude product obtained was dissolved in ethanol, acidified with saturated ethanolic hydrogen chloride solution and evaporated to give a residue which was crystallised from ethyl acetate to give 3-allyl 4-(3-[N-isopropylamino]propoxy)benzaldehyde hydrogen chloride (133 mg) as a solid, m.p. 109.1° C.; microanalysis, found; C, 62.6; H, 8.2; N, 4.6%; C16H23NO2. HCl 0.5H2O, C, 62.6; H, 8.1; N, 4.6%; NMR([CD3 ]12SO): 1.4-1.6(6H,d), 1.7-2.0(2H,m), 3.2-3.5(3H,m), 3.8-4.3(2H,m), 4.9-5.1(2H,m), 5.8-6.1(1H,m), 6.9-7.0(1H,d), 7.65-7.8(2H,m), 9.4-9.8(2H, br s) and 9.85(1H,s); m/z 262(M+H).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue purified by flash column chromatography on silica gel (Merck Art No 9385)
  3. additiona 90:8:2 (v/v/v) mixture of ethyl acetate/methanol/ammonia (density=0.88 g/cm 3) as eluent
  4. customThe crude product obtained
  5. customevaporated
  6. customto give a residue which
  7. customwas crystallised from ethyl acetate

Sources & evidence

ORD record
ord-8eab23d56fe248468b0b4d9f37562e94
Source dataset
uspto-grants-1999_02
Patent number
US05866611

Reaction notes

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