Propanal → HCID 20426685, compound

HRID 615778Notes

Reaction equation

HRID 615778 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[CH2:15][CH:14]([N:19]=[N+]=[N-])[CH2:13][CH2:12][C:11]=2[C:10]=1[C:22]([NH2:24])=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN.[CH2:28](OC1C=CC2CC(N)CCC=2C=1C(N)=O)[C:29]1C=CC=C[CH:30]=1.[CH:50](=O)[CH2:51][CH3:52].C([BH3-])#N.[Na+].C(Cl)(Cl)[Cl:59].CO.CC(C)=O.[OH-].[NH4+]>C1COCC1.C(O)C.[Ni]>[ClH:59].[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[CH2:15][CH:14]([N:19]([CH2:50][CH2:51][CH3:52])[CH2:28][CH2:29][CH3:30])[CH2:13][CH2:12][C:11]=2[C:10]=1[C:22]([NH2:24])=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 6

HCID 527PropanalHCID 24654Hydrazine hydrate (1:1)HCID 5003444Sodium cyanoborohydrideHCID 13318640HCID 13318640, compoundHCID 13318643HCID 13318643, compoundHCID 86739412HCID 86739412, compound

Product 1

HCID 20426685HCID 20426685, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
0 °C

Procedure

Alternatively, 0.5 g of dl-2-benzyloxy-6-azido-5,6,7,8-tetrahydro-1-naphthalenecarboxamide were dissolved in 100 ml. of a 1:1 THF/ethanol solvent mixture. About 1 g. of Raney nickel were added and the mixture stirred at about 0° C. while 5 ml. of hydrazine hydrate were added thereto in dropwise fashion. After the addition had been completed, the reaction mixture was stirred for 4 hours at ambient temperature after which time it was filtered. The solvent was removed from the filtrate leaving a yellow residue. TLC indicated a single spot with Rf =0.63 using a 63:7:27:3 chloroform/methanol/acetone/ammonium hydroxide solvent system. Yield of dl-2-benzyloxy-6-amino-5,6,7,8-tetrahydro-1-naphthalenecarboxamide was 0.46 g. (100%). This 0.46 g. sample was alkylated with propionaldehyde and sodium cyanoborohydride by the procedure of Example 1 to yield dl-2-benzyloxy-6-di-n-propylamino-5,6,7,8-tetrahydro-1-naphthalenecarboxamide hydrochloride. TLC (9:1 chloroform/methanol) Rf =0.40.

Workup

  1. additionAfter the addition
  2. stirringthe reaction mixture was stirred for 4 hours at ambient temperature after which time it
  3. filtrationwas filtered
  4. customThe solvent was removed from the filtrate
  5. customleaving a yellow residue

Sources & evidence

ORD record
ord-cea66e5deeb240b0a5056e329d821a54
Source dataset
uspto-grants-1985_02
Patent number
US04500545

Reaction notes

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