Diisopropylethylamine → HCID 57911617, compound

HRID 1694569Notes

Reaction equation

HRID 1694569 reaction equation
[CH:1](N(CC)C(C)C)(C)C.Cl.Cl.N1[CH2:17][CH2:16][C:15]2([C:25]3[C:20](=[N:21][CH:22]=[CH:23][CH:24]=3)[C:19](=[O:26])[O:18]2)[CH2:14][CH2:13]1.Cl.[CH3:28][N:29]([CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)[C:30](Cl)=[O:31]>C(Cl)(Cl)Cl>[CH3:28][N:29]([CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)[C:30]([CH:1]1[CH2:17][CH2:16][C:15]2([C:25]3[C:20](=[N:21][CH:22]=[CH:23][CH:24]=3)[C:19](=[O:26])[O:18]2)[CH2:14][CH2:13]1)=[O:31]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 468355837H-Spiro[furo[3,4-b]pyridine-5,4'-piperidin]-7-one--hydrogen chloride (1/2)HCID 86635012HCID 86635012, compound

Product 1

HCID 57911617HCID 57911617, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

With cooling with ice, N,N-diisopropylethylamine (10.6 mL) and N-methyl-2-piperidin-1-ylethanamine (7.10 g) were added in that order to chloroform (140 mL) solution of triphosgene (8.15 g). The reaction liquid was stirred for 1 hour with cooling with ice, and then water (25 mL) was added thereto. The reaction liquid was azeotroped with toluene and then dried overnight under reduced pressure to obtain methyl(2-piperidin-1-ylethyl)carbamyl chloride monohydrochloride (20.0 g) as a pale yellow oily substance. Not further purified, the compound was used in the next reaction. Chloroform (2.0 mL), N,N-diisopropylethylamine (0.342 mL), 7H-spiro[furo[3,4-b]pyridine-5,4′-piperidin]-7-one dihydrochloride (136 mg) were added to the obtained methyl(2-piperidin-1-ylethyl)carbamyl chloride monohydrochloride (100 mg), and stirred at 70° C. for 11 hours. The reaction liquid was concentrated under reduced pressure, and then purified through reversed-phase HPLC (0.1% TFA acetonitrile/H2O=5% to 50%, gradient) to obtain the entitled compound (57 mg, 24%) as a pale yellow oily substance.

Workup

  1. customNot further purified
  2. customthe compound was used in the next reaction
  3. customThe reaction liquid
  4. concentrationwas concentrated under reduced pressure
  5. custompurified through reversed-phase HPLC (0.1% TFA acetonitrile/H2O=5% to 50%, gradient)

Sources & evidence

ORD record
ord-f62151c630704ba78e738edb7053aaae
Source dataset
uspto-grants-2012_04
Patent number
US08158791B2

Reaction notes

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