4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → HCID 10078061, compound

HRID 346799Notes

Reaction equation

HRID 346799 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][C:6]([N:15]([CH3:17])[CH3:16])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.[K].[F:37][C:38]1[CH:39]=[C:40]2[C:44](=[CH:45][CH:46]=1)[NH:43][CH:42]=[C:41]2[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][C:52](O)=[O:53]>CO>[CH3:16][N:15]([CH3:17])[C:6]1([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:5][CH2:4][CH:3]([CH2:2][NH:1][C:52](=[O:53])[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][C:41]2[C:40]3[C:44](=[CH:45][CH:46]=[C:38]([F:37])[CH:39]=3)[NH:43][CH:42]=2)[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 5462222PotassiumHCID 21082140HCID 21082140, compoundHCID 21082146(4-Aminomethyl-1-phenylcyclohexyl)dimethylamine

Product 1

HCID 10078061HCID 10078061, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the diastereoisomers of (4-aminomethyl-1-phenylcyclohexyl)dimethylamine (347 mg, 1.49 mmol.) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (620 mg, 2.2 mmol.) was added to a solution of the potassium salt of 6-(5-fluoro-1H-indol-3-yl)hexanoic acid (430 mg, 1.49 mmol.) in abs. methanol (30 ml), and stirring was carried out for 3 d at RT. For working up, the mixture was concentrated, water (10 ml) and 2M HCl (15 ml) were added to the residue, and washing was carried out with ether (25 ml). The diethyl ether phase was separated off. The aqueous phase and oily drops contained therein were adjusted to pH 11 with 5M NaOH and extracted with EE (4×15 ml). The combined EE extracts were washed with 1M NaOH (2×2 ml), dried, filtered and concentrated. The residue was a diastereoisomeric mixture of the bases of the target product, which was separated by flash chromatography on silica gel (75 g) and purified (eluant: 1500 ml of methanol/EE 1:1). 192 mg of the non-polar diastereoisomer of 6-(5-fluoro-1H-indol-3-yl)hexanoic acid (4-dimethylamino-4-phenylcyclohexylmethyl)amide were obtained (m.p. 52–54° C.).

Workup

  1. concentrationthe mixture was concentrated
  2. additionwater (10 ml) and 2M HCl (15 ml) were added to the residue
  3. washwashing
  4. customThe diethyl ether phase was separated off
  5. extractionextracted with EE (4×15 ml)
  6. washThe combined EE extracts were washed with 1M NaOH (2×2 ml)
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. additiona diastereoisomeric mixture of the bases of the target product, which
  11. customwas separated by flash chromatography on silica gel (75 g)
  12. custompurified (eluant: 1500 ml of methanol/EE 1:1)

Sources & evidence

ORD record
ord-96dd4a254d37413983e154d6aa3b9c1d
Source dataset
uspto-grants-2007_02
Patent number
US07173045B2

Reaction notes

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