14-Bromo-1-tetradecanol → HCID 20482565, compound

HRID 648305Notes

Reaction equation

HRID 648305 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]Br.C([CH:19]1[CH2:23][CH2:22][CH2:21][N:20]1[C:24](=[O:32])[C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=1)C>CN(C)P(N(C)C)(N(C)C)=O>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:31][C:28]1[CH:27]=[CH:26][C:25]([C:24]([N:20]2[CH2:19][CH2:23][CH2:22][CH2:21]2)=[O:32])=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 275718214-Bromo-1-tetradecanolHCID 20482477HCID 20482477, compound

Product 1

HCID 20482565HCID 20482565, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 10 g. of 14-hydroxytetradecyl bromide and 10.8 g. of ethyl 1-(4-aminobenzoyl)pyrrolidine in 75 ml. hexamethylphosphoramide is heated at 110° C. for 17 hours. The cooled solution is diluted with 100 ml. water, filtered, and the residue is washed in portions with 100 ml. 50% ethanol-water. After drying the product is crystallized from ethanol to yield 1-[4-(14-hydroxytetradecylamino)benzoyl]pyrrolidine as a white solid.

Workup

  1. additionThe cooled solution is diluted with 100 ml
  2. filtrationwater, filtered
  3. washthe residue is washed in portions with 100 ml
  4. customAfter drying the product
  5. customis crystallized from ethanol

Sources & evidence

ORD record
ord-5af1e84967154b93a9ca23caeb9c40c4
Source dataset
uspto-grants-1983_10
Patent number
US04411903

Reaction notes

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