Potassium Carbonate → HCID 178495939, compound

HRID 2384539Notes

Reaction equation

HRID 2384539 reaction equation
Cl[CH2:2][C:3]([N:5]([CH2:7][CH:8]([O:11][CH3:12])[O:9][CH3:10])[CH3:6])=[O:4].[NH2:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>C(OCCCC)(=O)C>[OH:20][C@H:17]1[CH2:18][CH2:19][C@H:14]([NH:13][CH2:2][C:3]([N:5]([CH2:7][CH:8]([O:11][CH3:12])[O:9][CH3:10])[CH3:6])=[O:4])[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 128507002-Chloro-N-(2,2-dimethoxyethyl)-N-methylacetamideHCID 178511715HCID 178511715, compound

Product 1

HCID 178495939HCID 178495939, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 31272Butyl AcetateSolvent2×

Conditions

Temperature
65 °C

Procedure

50 g 2-chloro-N-(2,2-dimethoxy-ethyl)-N-methyl-acetamide in 100 ml n-butyl acetate are added dropwise to a suspension of 35.3 g trans-4-aminocyclohexanol and 53 g potassium carbonate in 150 ml n-butyl acetate at 90-100° C. within 2.5 h. After 45 min the suspension is filtered at 65° C. and washed with 70 ml of n-butyl acetate warmed to 65° C. 100 ml solvent are distilled off from the filtrate and the solution evaporated down is inoculated with product at 40° C. After 16 h at ambient temperature the precipitate is filtered off and washed with 70 ml tert-butylmethylether. After drying, 50 g product is obtained.

Workup

  1. filtrationAfter 45 min the suspension is filtered at 65° C.
  2. washwashed with 70 ml of n-butyl acetate
  3. distillation100 ml solvent are distilled off from the filtrate
  4. customthe solution evaporated down
  5. customis inoculated with product at 40° C
  6. filtrationAfter 16 h at ambient temperature the precipitate is filtered off
  7. washwashed with 70 ml tert-butylmethylether
  8. customAfter drying

Sources & evidence

ORD record
ord-d287b04d38c944feab986d54c181c0fe
Source dataset
uspto-grants-2012_09
Patent number
US08263768B2

Reaction notes

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