Propylamine → Ethyl 1-(propylcarbamoyl)cyclopropanecarboxylate

HRID 711801Notes

Reaction equation

HRID 711801 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:9]([OH:11])=O)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH2:12]([NH2:15])[CH2:13][CH3:14].C([O-])(O)=O.[Na+].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>CN(C=O)C>[CH2:12]([NH:15][C:9]([C:6]1([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][CH2:8]1)=[O:11])[CH2:13][CH3:14]

Participants

7

Reactant 5

HCID 7852PropylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 117894721-(Ethoxycarbonyl)cyclopropanecarboxylic acid

Product 1

HCID 66746001Ethyl 1-(propylcarbamoyl)cyclopropanecarboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(ethoxycarbonyl)cyclopropanecarboxylic acid (Wheeler, T. N.; Ray, J. A. Synthetic Communications 1988, 18(2), 141) (1.52 g, 9.62 mmol) and n-propylamine (0.63 g, 10.58 mmol) in anhydrous DMF (65 mL) at rt, were added NaHCO3 (4.04 g, 48.11 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (2.21 g, 11.54 mmol) and 1-hydroxybenzotriazole hydrate (1.77 g, 11.54 mmol) under a nitrogen atmosphere. After being stirred at rt overnight, the mixture was partitioned between water (100 mL) and EtOAc (300 mL). The organic phase was separated, washed with water and brine, and was dried over anhydrous MgSO4. The filtrate was evaporated to give 1.65 g (86%) of the crude product which was used in the next step without purification. 1H-NMR (400 MHz, DMSO-d6) δ 8.33 (broad s, 1H), 4.08 (q, J=6.8 Hz, 2H), 3.07 (q, J=6.4 Hz, 2H), 1.43 (hex, J=6.4 Hz, 2H), 1.31 (s, 4H), 1.17 (t, J=6.4 Hz, 3H), 0.85 (t, J=7.2 Hz, 3H).

Workup

  1. customthe mixture was partitioned between water (100 mL) and EtOAc (300 mL)
  2. customThe organic phase was separated
  3. washwashed with water and brine
  4. dry with materialwas dried over anhydrous MgSO4
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-be9e44e73f644541a1fbbb66de813392
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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