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Methanol → 3-(4-Methoxybenzylamino)-4-hydroxy-alpha-(tert-butylaminomethyl)benzyl alcohol hydrochloride

HRID 616212
Notes
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Reaction equation

HRID 616212 reaction equation
[ClH:1].[NH2:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[OH:17])[CH:6]([OH:13])[CH2:7][NH:8][C:9]([CH3:12])([CH3:11])[CH3:10].[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1.CO>O=[Pt]=O.O>[ClH:1].[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH:2][C:3]2[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=2[OH:17])[CH:6]([OH:13])[CH2:7][NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:22][CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 887MethanolHCID 312444-MethoxybenzaldehydeHCID 13416921HCID 13416921, compound

Product 1

HCID 1629243-(4-Methoxybenzylamino)-4-hydroxy-alpha-(tert-butylaminomethyl)benzyl alcohol hydrochloride

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst
HCID 962
Water
Solvent

Procedure

A mixture of 3-amino-4-hydroxy-α-(tert.butylaminomethyl)-benzylalcohol hydrochloride (6.53 g, 0.025 mole), p-methoxybenzaldehyde (3.4 g, 0.025 mole), PtO2 (180 mg), and methanol (125 ml) was placed in a hydrogenation apparatus and hydrogenated at normal pressure (20 - 30 cm H2O superatmospheric) for one hour and 50 minutes. During this period of time, the calculated amount of hydrogen was absorbed, and the hydrogenation was interrupted by supplying argon. The platinum catalyst was filtered off with continued supply of argon, but in spite of this, the filtrate quickly became dark due to oxidation. The filtrate was immediately evaporated in vacuum at 40° - 50° C. The residue which was a light brown foam (9.53 g), was recrystallized twice by precipitation from ethanol/ether (1:1). The yield of the analytical pure 3-(4-methoxybenzylamino)-4-hydroxy-α-(tert.butylaminomethyl)benzylalcohol hydrochloride was 5.2 g (55%), m.p. 196.6° - 197.8° C.

Workup

  1. waitDuring this period of time
  2. customthe calculated amount of hydrogen was absorbed
  3. filtrationThe platinum catalyst was filtered off with continued supply of argon
  4. customThe filtrate was immediately evaporated in vacuum at 40° - 50° C
  5. customwas recrystallized twice by precipitation from ethanol/ether (1:1)

Sources & evidence

ORD record
ord-90df2bbbc53547ccb0f9b0244b9ec91a
Source dataset
uspto-grants-1978_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04072760

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes