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Isopropylamine → Tert-butyl 4-[2-(isopropylamino)-2-oxoethyl]piperidine-1-carboxylate

HRID 1241421
Notes
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Reaction equation

HRID 1241421 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([OH:17])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[N:19]1[C:23]2[CH:24]=CC=C[C:22]=2N=N1.Cl.CN(C)CCCN=C=NCC.CN1CCOCC1.C(N)(C)C>CN(C=O)C>[CH:23]([NH:19][C:15](=[O:17])[CH2:14][CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]1)([CH3:24])[CH3:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 6363IsopropylamineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 1512539[1-(tert-Butoxycarbonyl)piperidin-4-yl]acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 21934696
Tert-butyl 4-[2-(isopropylamino)-2-oxoethyl]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

[1-(Tert-butoxycarbonyl)piperidin-4-yl]acetic acid 46-1 (0.20 g, 0.82 mmol), 1-hydroxybenzotriazole (0.15 g, 0.99 mmol), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.21 g, 1.07 mmol), 4-methylmorpholine (0.33 g, 3.29 mmol) and isopropyl amine (0.053 g, 0.90 mmol) were dissolved in DMF and stirred at 25° C. for 18 hours. Evaporated off the DMF and partitioned between ethyl acetate and dilute KHSO4. The aqueous was drawn off and the organic was washed with dilute NaHCO3, brine, dried, filtered and evaporated to afford 46-2. 1H-NMR (CD3OD): 4.03(d, 2H); 3.95(m, 1H); 2.75(br s, 2H); 2.06(d, 2H); 1.91(m, 1H); 1.64 (d, 2H); 1.44(s, 9H); 1.12(complex, 8H).

Workup

  1. customEvaporated off the DMF
  2. custompartitioned between ethyl acetate and dilute KHSO4
  3. washthe organic was washed with dilute NaHCO3, brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customto afford 46-2

Sources & evidence

ORD record
ord-c684617ec1654db5bf17ace43eeff7dc
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07115597B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes