Hydrochloric Acid → Morpholin-4-yl-[4-(2-pyrrolidin-2-ylethyl)naphthalen-1-yl]methanone

HRID 81391Notes

Reaction equation

HRID 81391 reaction equation
[N:1]1[CH2:5][CH2:4][CH2:3][C:2]=1[CH2:6][CH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[O:19])=[CH:10][CH:9]=1.C([BH3-])#N.[Na+].Cl.[OH-].[Na+]>CO>[N:20]1([C:18]([C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:8]([CH2:7][CH2:6][CH:2]3[CH2:3][CH2:4][CH2:5][NH:1]3)=[CH:9][CH:10]=2)=[O:19])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 58483951{4-[2-(4,5-dihydro-3H-pyrrol-2-yl)ethyl]naphthalen-1-yl)morpholin-4-ylmethanone

Product 1

HCID 58483889Morpholin-4-yl-[4-(2-pyrrolidin-2-ylethyl)naphthalen-1-yl]methanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6.4 1 g of {4-[2-(4,5-dihydro-3H-pyrrol-2-yl)ethyl]naphthalen-1-yl)morpholin-4-ylmethanone is dissolved in 50 ml of methanol, and 0.26 g of sodium cyano borohydride is added. A pH of 2 inset at 0° C. using methanolic HCl. The mixture is subsequently allowed to left to stir at RT for a further 6 h and then subjected to aqueous work-up. A pH of 9 is set using aqueous NaOH, and the mixture is extracted with ethyl acetate. The dried and evaporated organic phase is purified by chromatography, giving 460 mg of morpholin-4-yl-[4-(2-pyrrolidin-2-ylethyl)naphthalen-1-yl]methanone; Rt.: 1.420 min; [M+H]+339.2.

Workup

  1. custominset at 0° C.
  2. waitto left
  3. extractionthe mixture is extracted with ethyl acetate
  4. customThe dried
  5. customevaporated organic phase
  6. customis purified by chromatography

Sources & evidence

ORD record
ord-206c27b47eea4dabbc9ce22ef25b789d
Source dataset
uspto-grants-2014_09
Patent number
US08846694B2

Reaction notes

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