Sodium borohydride → HCID 9954184, compound

HRID 2108050Notes

Reaction equation

HRID 2108050 reaction equation
[BH4-].[Na+].[NH2:3][C:4]1[C:9]([Cl:10])=[CH:8][C:7]([C:11](=[O:29])[CH2:12][NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[CH:6][C:5]=1[Cl:30]>CO>[NH2:3][C:4]1[C:9]([Cl:10])=[CH:8][C:7]([CH:11]([CH2:12][NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[OH:29])=[CH:6][C:5]=1[Cl:30]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23045059HCID 23045059, compound

Product 1

HCID 9954184HCID 9954184, compoundYield 10.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.16 g) was added portionwise over 5 min to a solution of 1-(4-amino-3,5-dichlorophenyl)-2-[[6-[2-(2-pyridinyl)ethoxy]hexyl]amino]ethanone (0.44 g) in methanol (7 ml) at 0°-5° with stirring. After 1.5 h, the solution was evaporated in vacuo and the residue partitioned between water (60 ml) and ethyl acetate (100 ml). The organic phase was dried and evaporated in vacuo to a gum which was purified by FCC eluting with System C (90:10:1) to afford a product, which was triturated with hexane (2 ml) to give the title compound as a colourless powder (47 mg), m.p. 94.5°-96.5°, t.l.c. (System A 39:10:1) Rf 0.44.

Workup

  1. customthe solution was evaporated in vacuo
  2. customthe residue partitioned between water (60 ml) and ethyl acetate (100 ml)
  3. customThe organic phase was dried
  4. customevaporated in vacuo to a gum which
  5. customwas purified by FCC
  6. washeluting with System C (90:10:1)
  7. customto afford a product, which
  8. customwas triturated with hexane (2 ml)

Sources & evidence

ORD record
ord-e4132a704453471696b0706a5dad61bb
Source dataset
uspto-grants-1990_06
Patent number
US04937251

Reaction notes

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