HCID 18974541, compound → HCID 18974556, compound

HRID 2394985Notes

Reaction equation

HRID 2394985 reaction equation
Cl.[CH3:2][N:3]([CH3:20])[CH2:4][CH:5]([CH3:19])[C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)(O)[CH:7]([CH3:9])[CH3:8]>C(O)=O>[CH3:18][O:17][C:13]1[CH:12]=[C:11]([C:6](=[C:7]([CH3:8])[CH3:9])[CH:5]([CH3:19])[CH2:4][N:3]([CH3:20])[CH3:2])[CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 1

HCID 18974541HCID 18974541, compound

Product 1

HCID 18974556HCID 18974556, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Starting from (RS)-1-dimethylamino-2,4-dimethyl-pentan-3-one and 1-bromo-3-methoxy-benzene, (2RS,3RS)-1-dimethylamino-3-(3-methoxy-phenyl)-2,4-dimethyl-pentan-3-ol hydrochloride (26) was obtained, under the conditions given in Example 1 (1st step), in a yield of 44% and with a melting point of 180°-181° C. 30 g (0.1 mole) of compound (26) were reacted with 450 ml of concentrated formic acid as in Example 5. The crude base obtained was introduced on to a column packed with silica gel. Elution with 7:1 diisopropyl ether/methanol gave 19 g base (77% theoretical) as a light yellow, viscous oil.

Workup

  1. customThe crude base obtained
  2. additionwas introduced on to a column
  3. washElution with 7:1 diisopropyl ether/methanol

Sources & evidence

ORD record
ord-07e5d6cd1f5243fc838df8b0431c9653
Source dataset
uspto-grants-1998_09
Patent number
US05811582

Reaction notes

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