4-Morpholinecarbonyl chloride → HCID 118037455, compound

HRID 715586Notes

Reaction equation

HRID 715586 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.[N:18]1([C:24](Cl)=[O:25])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>N1C=CC=CC=1>[N:18]1([C:24]([O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])[CH2:6][CH2:7]2)=[O:25])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 848104-Morpholinecarbonyl chloride3×HCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylate

Product 1

HCID 118037455HCID 118037455, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

Benzyl 4-hydroxypiperidine-1-carboxylate (65 μL) is dissolved in pyridine (2 mL), treated with morpholine-4-carbonyl chloride (500 μL) and stirred for 6 hours at 50° C. Morpholine-4-carbonyl chloride (75 μL) is added and the mixture is stirred for 12 hours at 80° C. Again morpholine-4-carbonyl chloride (500 μL) is added and the mixture is stirred for 12 hours at 80° C. The mixture is partitioned between ethylacetate and hydrochloric acid (1 M). The organic phase is dried (MgSO4) and concentrated. The residue is purified by HPLC on reversed phase to give the title compound. LC (method 1): tR=0.96 min; Mass spectrum (ESI+): m/z=349 [M+H]+.

Workup

  1. stirringthe mixture is stirred for 12 hours at 80° C
  2. stirringthe mixture is stirred for 12 hours at 80° C
  3. customThe mixture is partitioned between ethylacetate and hydrochloric acid (1 M)
  4. dry with materialThe organic phase is dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue is purified by HPLC on reversed phase

Sources & evidence

ORD record
ord-d81f05a0ce014453b6e63888ebffa314
Source dataset
uspto-grants-2015_11
Patent number
US09187477B2

Reaction notes

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