4-Methylmorpholine → 4-[3-(1-Ethoxycarbonyl-1-methyl-ethoxy)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester

HRID 502385Notes

Reaction equation

HRID 502385 reaction equation
[CH2:1]([O:3][C:4]([C:6]([CH3:18])([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=O)[CH3:7])=[O:5])[CH3:2].ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.[C:37]([O:41][C:42]([N:44]1[CH2:49][CH2:48][CH:47]([NH2:50])[CH2:46][CH2:45]1)=[O:43])([CH3:40])([CH3:39])[CH3:38]>CC#N>[C:37]([O:41][C:42]([N:44]1[CH2:49][CH2:48][CH:47]([NH:50][C:12](=[O:14])[C:11]2[CH:15]=[CH:16][CH:17]=[C:9]([O:8][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])([CH3:7])[CH3:18])[CH:10]=2)[CH2:46][CH2:45]1)=[O:43])([CH3:40])([CH3:38])[CH3:39]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 12682914-Amino-1-Boc-piperidineHCID 219357143-(1-Ethoxycarbonyl-1-methyl-ethoxy)-benzoic acid

Product 1

HCID 684578994-[3-(1-Ethoxycarbonyl-1-methyl-ethoxy)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl esterYield 100.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

1.30 g (5.0 mmol) of 3-(1-ethoxycarbonyl-1-methyl-ethoxy)-benzoic acid [U.S. Pat. Appl. Publ. (2005), 89 pp. US 2005096337 A1] and 0.969 g (5.25 mmol) of 2-chloro-4,6-dimethoxy-1,3,5-triazine were dissolved under argon in 5 mL of MeCN and cooled down to 0° C.; then, 1.10 mL (1.064 g=2.0 eq.) of N-methylmorpholine was added and the mixture was stirred at 0° C. for 2 h. To this mixture was added 1.277 g (6.0 mmol) 4-amino-piperidine-carboxylic acid tert-butyl ester in small portions; afterwards the reaction was then warmed up to rt. After stirring for 16 h, it was poured into crashed ice and extracted twice with MeCl2; the organic phases were washed with water, dried over MgSO4, filtered and evaporated i.V. to yield 2.18 g of the crude title compound as off-white solid. MS: 435.2 (MH+).

Workup

  1. temperatureafterwards the reaction was then warmed up to rt
  2. stirringAfter stirring for 16 h
  3. additionit was poured
  4. extractionextracted twice with MeCl2
  5. washthe organic phases were washed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated i.V

Sources & evidence

ORD record
ord-d9e2601c9d5a41b2b6f4866487b8948e
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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