Formaldehyde → HCID 67684703, compound

HRID 342216Notes

Reaction equation

HRID 342216 reaction equation
[CH2:1]([N:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]([C:23]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=1)[NH:18][CH2:17][CH2:16]2)[CH3:5])[CH:2]=[CH2:3].[CH2:30]=O.[OH-].[Na+]>O1CCOCC1>[CH2:1]([N:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]([C:23]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=1)[N:18]([CH3:30])[CH2:17][CH2:16]2)[CH3:5])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 67684370HCID 67684370, compound

Product 1

HCID 67684703HCID 67684703, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

0.1 g of (RS)-allyl-[6-[1-(4-bromo-phenyl)-1,2,3,4-tetra-hydro-isoquinolin-6-yloxy]-hexyl]-methyl-amine (Ex. 21) is taken up in 2 ml of a 1M NaH2PO3 solution and treated with 2 ml of dioxan as a solubilizer. After the addition of 2 ml of a 37% aqueous formaldehyde solution the mixture is heated to 65° C. for 48 hrs. For the working-up, the mixture is adjusted to pH >12 with 4M aqueous sodium hydroxide solution and extracted with ethyl acetate. After evaporation of the extracts and chromatography of the residue (silica gel, toluene/acetone/triethylamine, 25:74:1) there is obtained 0.12 g of (RS)-allyl-[6-[1-(4-bromo-phenyl)-2-methyl-1,2,3,4-tetrahydro-isoquinolin-6-yloxy]-hexyl]-methyl-amine which is converted into its hydrochloride, MS: m/e 471 (M+H+, 1 Br).

Workup

  1. extractionextracted with ethyl acetate
  2. customAfter evaporation of the extracts and chromatography of the residue (silica gel, toluene/acetone/triethylamine, 25:74:1) there

Sources & evidence

ORD record
ord-dc6f41bf98d54de28eb7dcdba8e775f6
Source dataset
uspto-grants-1999_01
Patent number
US05856503

Reaction notes

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