Succinic anhydride → HCID 551031, compound

HRID 327801Notes

Reaction equation

HRID 327801 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[CH2:8]([N:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[CH3:9]>CC#N>[CH3:11][N:10]([CH2:8][C:9]#[C:9][CH2:8][N:10]1[CH2:13][CH2:14][CH2:12][CH2:11]1)[C:1](=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 8471Triethylamine

Product 1

HCID 551031HCID 551031, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Intermediate compount 004 (557 mg, 3.66 mmol) was added to a solution of succinic anhydride (330 mg, 3.30 mmol) and triethylamine (20.51 mL, 3.66 mmol) in MeCN was removed under a stream of N2, and the crude product was chromatographed on a silica gel column (CHCl3 /MeOH/AcOH, 10/10/1) to give N-Methyl-N-[4-(1-pyrrolidinyl)-2-butynyl]-3-carboxypropanamide as a light brown solid. MS (CI-NH3), m/e 253 (MH+); TLC (CHCl3 /MeOH/AcOH: 10/10/1), Rf 0.34; 1H NMR (CDCl3) δ1.82 (br s, 4 H), 2.48 (t, J=5.8 Hz, 2 H), (t, J=5.8 Hz, 2 H), 2.68 (br s, 4 H), 2.93 & 3.06* (s, 3 H), 3.44 (s, 2 H), 4.11 & 4.21* (s, 2 H).

Workup

  1. customwas removed under a stream of N2
  2. customthe crude product was chromatographed on a silica gel column (CHCl3 /MeOH/AcOH, 10/10/1)

Sources & evidence

ORD record
ord-1d639af4ea8c40dc91f38a6e3cf91c77
Source dataset
uspto-grants-1993_12
Patent number
US05274121

Reaction notes

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