Ammonium Chloride → HCID 69134565, compound

HRID 917684Notes

Reaction equation

HRID 917684 reaction equation
[Mg].Br[C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH3:14])[CH:9]=2)[CH:4]=1.[CH2:15]([O:22][CH:23]1[CH2:28][CH2:27][C:26](=[O:29])[CH:25]([CH2:30][N:31]([CH3:33])[CH3:32])[CH2:24]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Cl-].[NH4+]>C1COCC1>[CH2:15]([O:22][CH:23]1[CH2:28][CH2:27][C:26]([C:3]2[CH:12]=[CH:11][C:10]3[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH3:14])[CH:9]=3)[CH:4]=2)([OH:29])[CH:25]([CH2:30][N:31]([CH3:33])[CH3:32])[CH2:24]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 787862-Bromo-6-methoxynaphthaleneHCID 5462224MagnesiumHCID 10999837HCID 10999837, compound

Product 1

HCID 69134565HCID 69134565, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The corresponding Grignard reagent was produced in 11 ml THF p.a. from 0.28 g magnesium and 2.72 g 2-bromo-6-methoxynaphthalene, a solution of 2.00 g 4-benzyloxy-2-dimethylaminomethylcyclohexanone in 8 ml THF p.a. added dropwise with ice cooling, and the mixture stirred for 1 hour. For working up, 4 ml 4 M ammonium chloride solution were added to the ice bath, the organic phase separated off, the aqueous phase extracted twice with diethyl ether, the combined organic phases dried by sodium sulphate, filtered and concentrated. The crude product obtained (3.20 g) was chromatographed with ethyl acetate/methanol/hexane (V/V/V=1:1:1) on silica gel. 1.52 g 4-benzyloxy-2-dimethylaminomethyl-1-(6-methoxynaphthalen-2-yl)cyclohexanol were obtained and converted into the corresponding hydrochloride (1.32 g) in the same way as in AAV 1.

Workup

  1. additionadded dropwise with ice cooling
  2. customthe organic phase separated off
  3. extractionthe aqueous phase extracted twice with diethyl ether
  4. dry with materialthe combined organic phases dried by sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product obtained (3.20 g)
  8. customwas chromatographed with ethyl acetate/methanol/hexane (V/V/V=1:1:1) on silica gel

Sources & evidence

ORD record
ord-55ba57b8eb7c4ae49047ea4d02fd3f6f
Source dataset
uspto-grants-2007_09
Patent number
US07273952B2

Reaction notes

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