Water → HCID 66782272, compound

HRID 1095456Notes

Reaction equation

HRID 1095456 reaction equation
[NH2:1][C:2]1([CH2:13][OH:14])[C:10]2[C:5](=[CH:6][C:7]([O:11][CH3:12])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[Cl:22][CH2:23][C:24](Cl)=[O:25].O>C(#N)C.CO>[Cl:22][CH2:23][C:24]([NH:1][C:2]1([CH2:13][OH:14])[C:10]2[C:5](=[CH:6][C:7]([O:11][CH3:12])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1)=[O:25]

Participants

7

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 66782011HCID 66782011, compound

Product 1

HCID 66782272HCID 66782272, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 60.0 mmol of (1-amino-5-methoxyindan-1-yl)methanol in 120 ml of acetonitrile and 40 ml of methanol is cooled to −10° C. and 69 mmol of triethylamine and, dropwise over the course of 1 hour, 80.5 mmol of chloroacetyl chloride are successively added. The reaction mixture is warmed to room temperature and stirred for 3 hours. The reaction mixture is poured into water and extracted with tert-butyl methyl ether. The combined organic phases are washed with brine, dried with sodium sulphate and evaporated. The title compound is obtained as a beige solid which is employed without further purification for the next stage. Rf=0.15 (ethyl acetate-heptane 1:1); Rt=3.01 (gradient I).

Workup

  1. extractionextracted with tert-butyl methyl ether
  2. washThe combined organic phases are washed with brine
  3. dry with materialdried with sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-2b38ccbc58e843bbbbbbe91054e3230a
Source dataset
uspto-grants-2012_03
Patent number
US08138179B2

Reaction notes

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